메뉴 건너뛰기
Synlett
Volumn , Issue 13, 2007, Pages 2061-2064
A new facile synthesis of 1,1-dibromo-2-arylethenes
Author keywords

1,1 dibromo 1 alkenes; Bromodesilylation; Halogenation; Organometallic reagents; Silicon derivatives
Indexed keywords

1,1 DIBROMO 2 ARYLETHENE; ETHYLENE; ORGANOMETALLIC COMPOUND; SILICON DERIVATIVE; UNCLASSIFIED DRUG;
EID: 34548179122     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-984901     Document Type: Article
Times cited : (19)
References (36)
  • 34
    • 34548163568 scopus 로고    scopus 로고
    • A Typical Procedure for the Synthesis of 1,1-Dibromo-2-arylethenes and Spectroscopic Data of Selected Products: N-Bromosuccinimide (3.55 g, 20 mmol) was added to the solution of the corresponding 1,1-bis(silyl)-2- arylethene (2 mmol) in anhyd MeCN (20 mL) and the suspension was stirred at r.t. for the appropriate time (see Table 1, The solvent was then evaporated and the mixture was extracted with n-hexane (50 mL, After extraction with an aqueous solution of Na2S2O3 (5, 50 mL) the organic layer was concentrated and the crude product was preloaded on to silica. 1,1-Dibromo-2-arylethenes were purified by silica chromatography, eluting with n-hexane-EtOAc (25:1, 1,1-Dibromo-2-(3-methoxyphenyl)ethene (4, yield: 0.514 g, 88, yellowish oil. 1H NMR (CDCl3, δ, 3.86 (3 H, Me, 6.88-6.96 (m, 2 H, 7.30-7.34 (m, 1 H, 7.60 (s, 1 H, CH, 7.68-7.72 (m, 1 H, 13C NMR CDCl3
    • 3: 339.7921; found: 339.7930.
  • 35
    • 34548179831 scopus 로고    scopus 로고
    • Synthesis of 1,4-Bis(2,2-dibromoethenyl)benzene (10, N-Bromosuccinimide (3.55 g, 20 mmol) was added to the solution of 1,4-bis[2,2-bis(trimethylsilyl)ethenyl]benzene (0.418 g, 1 mmol) in anhyd MeCN (50 mL) and the suspension was stirred at r.t. for 24 h. The solvent was then evaporated and the mixture was extracted with n-hexane (50 mL, After extraction with aqueous solution of Na2S2O3 (5, 50 mL) the organic layer was concentrated and the crude product was preloaded onto silica. 1,4-Bis(2,2-di-bromoethenyl)benzene was purified by silica gel chromatography, eluting with n-hexane-EtOAc (25:1, 0.397 g, 89, white crystals; mp 108-109°C, 1H NMR (CDCl3, δ, 7.39 (s, 2 H, CH, 7.68 (s, 4 H, Ar, 13C NMR (CDCl 3, δ, 90.4, CBr2, 128.4, 132.3 (Ar, 136.2 (CH, MS (EI, m/z, rel. int, 446 (100, M, 365 (12, 286 (30, 206 18, 12
    • 4: 445.7162; found: 445.7176.
  • 36
    • 34548189996 scopus 로고    scopus 로고
    • Synthesis of 1,4-Bis[2,2-bis(trimethylsilyl)ethenyl] benzene (9, A mixture consisting of palladium(II) acetate (67.0 mg, 0.30 mmol, triphenylphosphine (157.2 mg, 0.6 mmol, silver nitrate (1.70 g, 10 mmol, 1,4-diiodobenzene (5 mmol, 1,1-bis(trimethylsilyl)ethane (10 mmol, 1.72 g, triethylamine (2.80 mL, 20 mmol) and acetonitrile (30 mL) was placed in a 50-mL, two-necked, round-bottomed flask equipped with a magnetic stirring bar and reflux condenser. The suspension was heated in an oil-bath at 80°C for 2 h. After cooling to r.t, the reaction mixture was added to H2O (50 mL) and extracted with pentane (2 x 30 mL, The combined organic layers were dried (MgSO4) and the crude product obtained was then purified by column chromatography (silica gel, pentane) to give the pure product (2.01 g, 96, as white crystals. 1H NMR (CDCl3, δ, 0.01 (s, 18 H, SiMe, 0.18 (s, 18 H, SiMe, 7.12 (s, 4 H, Ar, 7.72 s, 2 H, CH, 13
    • 4: 418.2363; found: 418.2348.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.