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Volumn , Issue 13, 2009, Pages 2180-2182

The first synthesis of diethyl α,α- chlorofluorobenzylphosphonates

Author keywords

Chlorination; Diethyl , chlorofluorobenzylphosphonates; Fluorinated phosphonates; Fluorination

Indexed keywords

DIETHYL A,A CHLOROFLUOROBENZYLPHOSPHONATE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 68949130177     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217564     Document Type: Article
Times cited : (5)

References (37)
  • 30
    • 68949084032 scopus 로고    scopus 로고
    • General Procedure for the Preparation of α- Chlorobenzylphosphonates from α-Hydroxyphosphonates A solution of 1k (1.00 g, 3.46 mmol, 1.0 equiv) and Ph3P (1.36 g, 5.19 mmol, 1.5 equiv) in dry CCl4 (10 mL) is refluxed for 8 h under argon. Then, the mixture is evaporated under reduced pressure, and the semisolid residue is extracted with PE. The combined extracts are filtered, and the solvent is removed under reduced pressure. The crude material was purified by flash column chromatography on silica gel to yield 3k as yellow oil (0.81 g, 76, 1H NMR (300 MHz, CDCl3, δ, 1.26 (t, J, 7.0 Hz, 3 H, 1.35 (t, J, 7.0 Hz, 3 H, 4.00-4.14 (m, 2 H, 4.15-4.28 (m, 2 H, 5.00 (d, 2JPH, 15.2 Hz, 1 H, 7.73 (d, J, 8.6 Hz, 2 H, 8.25 (d, J, 8.6 Hz, 2 H) ppm. 13C NMR (75 MHz, CDCl3, δ, 16.2 d, 3JPC
    • PC = 7.0 Hz), 123.6, 129.8, 141.4, 148.0 ppm.
  • 31
    • 68949108928 scopus 로고    scopus 로고
    • General Procedure for the Preparation of α,α- Chlorofluorobenzylphosphonates from α-Chlorophosphonates To a solution of the α-chlorophosphonates 3k (0.31 g, 0.94 mmol, 1.0 equiv) in dry THF (10 mL) at -78°C was added dropwise a solution of NaHMDS (1.69 mmol, 2.0 M in THF, 1.5 equiv) in dry THF (5 mL) under argon. The resulting dark green solution was stirred for 1 h at -78°C. A solution of NFSI (0.41 g, 1.31 mmol, 1.3 equiv) in dry THF (5 mL) was added over a period of 10 min. After addition, the solution was stirred for 1 h and then allowed to warm to -30°C. The reaction was quenched with 0.01 N HC1, and the resulting solution was extracted with CH2Cl2. The combined organic layer was dried over MgSO4, and the solvent was removed under reduced pressure. The crude material was purified via flash column chromatography on silica gel to yield 4k as yellow oil (0.24 g, 77, 1H NMR 300 MHz
    • PF = 88.1 Hz) ppm.
  • 37
    • 68949089099 scopus 로고    scopus 로고
    • We thank one of the reviewers for pointing out these possibilities
    • We thank one of the reviewers for pointing out these possibilities.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.