SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 14, 2007, Pages 2227-2231

Facile preparation of 2-iodophenyl trifluoromethanesulfonates: Superior aryne precursors

(2) Ganta, Ashok a Snowden, Timothy S a

a UNIVERSITY OF ALABAMA (United States)

Author keywords

Arynes; Carbamate; Halogenation; Iodophenyl triflate; Metalations

Indexed keywords

2 IODOPHENYL TRIFLUOROMETHANESULFONATE; CARBAMIC ACID DERIVATIVE; N ISOPROPYL CARBAMATE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; HALOGENATION; IODINATION; LITHIATION;

EID: 34548805830 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-985565 Document Type: Article

Times cited : (9)

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36
- 34548736531
- General Procedure for the Preparation of 2-Iodophenols 11-20 To a solution of the carbamate (2.5 mmol) dissolved in dry Et2O (25 mL) under argon was added TMEDA (1.1 equiv, 2.75 mmol) at 0°C. Then TMSOTf (1.1 equiv, 2.75 mmol) was slowly added to the solution and the reaction mixture was allowed to warm to r.t. over a period of 30 min. After cooling the solution to -78°C, TMEDA (2.0 equiv, 5.0 mmol) was added followed by the dropwise addition of n-BuLi or t-BuLi (2.0-2.5 equiv, 5.0-6.2 mmol, The reaction mixture was stirred for 1 h and was then treated with I2 (1.0 equiv, 2.5 mmol) dissolved in THF (3 mL, After reacting for 2 h, EtOH (0.25 mL) was added and the solvent was removed by rotary evaporation. The resultant residue was dissolved in EtOH (25 mL) and treated with 5 mL of aq 2 N NaOH 4 equiv, 10 mmol, The reaction proceeded for 2 h, after which the pH was adjusted to 6-8 with 2 N HCl. The aqueous layer was extracted with Et
- 3 (25 mL), then dried and filtered. Upon concentration, the resulting residue was purified using flash chromatography (hexane-EtOAc, 95:5 to 9:1) affording the desired 2-iodophenol.

37
- 34548752827
- 2O (3 x 5 mL). The combined organic layers were dried and concentrated. The crude material was then purified by flash chromatography (100% hexane to hexane-EtOAc, 98:2) or recrystallized from hexane to afford the desired 2-iodophenyl triflate.
- 2O (3 x 5 mL). The combined organic layers were dried and concentrated. The crude material was then purified by flash chromatography (100% hexane to hexane-EtOAc, 98:2) or recrystallized from hexane to afford the desired 2-iodophenyl triflate.

38
- 34548729137
- 3: 209.1052; found: 209.1056.
- 3: 209.1052; found: 209.1056.

39
- 34548779702
- 3: 223.1208; found: 223.1210.
- 3: 223.1208; found: 223.1210.

40
- 34548789028
- 2: 255.1259; found: 255.1259.
- 2: 255.1259; found: 255.1259.

41
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42
- 34548776980
- 2: 197.0852; found: 197.0853.
- 2: 197.0852; found: 197.0853.

43
- 34548801886
- 2: 197.0852; found: 197.0850.
- 2: 197.0852; found: 197.0850.

44
- 34548801340
- 2: 247.0820; found: 247.0824.
- 2: 247.0820; found: 247.0824.

45
- 34548809690
- 2: 247.0820; found: 247.0822.
- 2: 247.0820; found: 247.0822.

46
- 0001711311
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47
- 34548790682
- Compound is commercially available
- Compound is commercially available.

48
- 34548776415
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49
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50
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51
- 0035105946
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52
- 34548770060
- 5S: 411.9089; found: 411.9106.
- 5S: 411.9089; found: 411.9106.

53
- 34548712364
- 4S: 395.9140; found: 395.9142.
- 4S: 395.9140; found: 395.9142.

54
- 33748643421
- Qing, F. L.; Fan, J.; Sun, H. B.; Yue, X. J. J. Chem. Soc., Perkin Trans. 1 1997, 3053.
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55
- 34548759631
- Compound 25: recrystallization from hexane, white needles, mp 41-42°C. IR (neat, 2925 (w, 1583 (s, 1469 (s, 1425 (s, 1375 (m, 1247 (m, 1213 (s, 1172 (m, 1137 (m, 1031 (m, 885 (m, 833 (m, 798 (m, 761 (m) cm-1. 1H NMR (500 MHz, CDCl3, δ, 8.10 (d, J, 2.2 Hz, 1 H, 7.60 (dd, J, 2.2, 8.6 Hz, 1 H, 7.53 (td, J, 1.8, 3.3 Hz, 1 H, 7.46 (td, J, 1.6, 15.0 Hz, 2 H, 7.46 (d, J, 1.6, 4.8 Hz, 1 H, 7.42 (td, J, 1.9, 4.8 Hz, 1 H, 7.38 (d, J, 8.6 Hz, 1 H, 13C NMR (125 MHz, CDCl3, δ, 149.5, 143.0, 139.1, 137.9, 129.1, 128.6, 128.5, 127.2, 122.0, 118.7 [q, J(CF, 321.0 Hz, 89.4. HRMS EI, m/z [M, calcd for C13H8F3IO3S: 427.9191; found: 427.9190
- 3S: 427.9191; found: 427.9190.

56
- 34548742872
- 3S: 385.8488; found: 385.8497.
- 3S: 385.8488; found: 385.8497.

57
- 34548740194
- 3S: 369.8772; found: 369.8778.
- 3S: 369.8772; found: 369.8778.

58
- 34548790116
- Compound 28: viscous liquid. IR (neat, 3154 (w, 1577 (m, 1457 (s, 1428 (s, 1281 (w, 1248 (m, 1220 (s, 1139 (s, 1096 (w, 1035 (w, 975 (s, 906 (s, 835 (m, 787 (m, 725 (s) cm-1. 1H NMR (500 MHz, CDCl3, δ, 7.43 (dt, J, 8.4, 6.1 Hz, 1 H, 7.16 (d, J, 8.4 Hz, 1 H, 7.11 (ddd, J, 8.3, 7.2, 1.2 Hz, 1 H, 13C NMR (125 MHz, CDCl3, δ, 163.0 [d, J(CF, 252.6 Hz, 151.0 [d, J(CF, 4.5 Hz, 130.7 [d, J(CF, 9.0 Hz, 118.7 [q, J(CF, 320.7 Hz, 117.7 [d, J(CF, 2.8 Hz, 115.3 [d, J(CF, 24.2 Hz, 79.2 [d, J(CF, 29.5 Hz, HRMS EI, m/z [M, calcd for C7H3F 4IO3S: 369.8784; found: 369.8783
- 3S: 369.8784; found: 369.8783.

59
- 34548752294
- Compound 29: recrystallization from hexane, white needles, mp 37-38°C. IR (neat, 3154 (w, 1606 (s, 1479 (s, 1430 (s, 1398 (m, 1323 (m, 1246 (m, 1221 (m, 1140 (m, 1181 (m, 1080 (m, 1023 (m, 906 (m, 829 (m, 808 (m, 735 (m) cm-1. 1H NMR (500 MHz, CDCl 3, δ, 8.08 (d, J, 8.3 Hz, 1H, 7.54 (d, J =1.3 Hz, 1 H, 7.38 (dd, J, 8.3, 1.7 Hz, 1 H, 13C NMR (125 MHz, CDCl3, δ, 150.3, 141.6, 132.9 [q, J (CF, 34.2 Hz, 126.1 [q, J(CF, 3.5 Hz, 122.7 [q, J(CF, 272.9 Hz, 119.1 [q, J(CF, 3.6 Hz, 118.7 [q, J(CF, 320.8 Hz, 94.1 [d, J(CF, 0.9 Hz, HRMS EI, m/z [M, Tf, calcd for C7H3F3IO: 286.9181; found: 286.9175
- 3IO: 286.9181; found: 286.9175.

60
- 34548730238
- 3IO: 286.9181; found: 286.9192.
- 3IO: 286.9181; found: 286.9192.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.