Thionyl Chloride → 2-Fluoro-5-methylbenzoyl chloride

HRID 2414378노트

반응식

HRID 2414378 반응식
[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:14])=O>>[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([Cl:14])=[O:5]

참가 물질

3

반응물 2

HCID 24386Thionyl ChlorideHCID 2428292-Fluoro-5-methylbenzoic acid

생성물 1

HCID 70180482-Fluoro-5-methylbenzoyl chloride

실험 절차

A mixture of 2-fluoro-5-methylbenzoic acid (41.05 g, 0.266 mol) in thionyl chloride (200 mL) is refluxed for 45 min., during which time it becomes homogeneous. After cooling, the thionyl chloride is evaporated to yield 2-fluoro-5-methylbenzoyl chloride, as a yellow liquid, which is dissolved in CH2Cl2 (500 mL), and cooled to 0° C. To this solution is added 2-(trimethylsilyl)-ethanol (48.65 mL, 40.14 g, 0.34 mol), followed by triethylamine (85.86 g, 118.3 mL, 0.85 mol), and the solution is warmed to room temp. over 1 h. The solution is then washed with 1 N HCl (2×500 mL), water (1×250 mL) and brine (1×100 mL), dried (MgSO4), evaporated and chromatographed (silica, 5% EtOAc/hexane) to yield (2-trimethylsilyl)-ethyl 2-fluoro-5-methylbenzoate, as a yellow oil.

후처리

  1. temperatureis refluxed for 45 min., during which time it
  2. temperatureAfter cooling
  3. customthe thionyl chloride is evaporated

출처 및 근거

ORD 기록
ord-3fa5f02955324033920d804052ccd055
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06812237B2

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