Toluene → Methyl 3-fluoro-4-methylbenzoate

HRID 220768

반응식

HRID 220768 반응식
S(Cl)(Cl)=O.[F:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:9]([OH:11])=[O:10].[C:16]1(C)C=CC=CC=1>>[CH3:16][O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:14]([CH3:15])=[C:6]([F:5])[CH:7]=1

참가 물질

4

반응물 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 676873-Fluoro-p-toluic acid

생성물 1

HCID 18973767Methyl 3-fluoro-4-methylbenzoate수율 83%

실험 절차

Thionyl chloride (9.62 g, 81 mmol) was added to a solution of 3-fluoro-4-methylbenzoic acid (5.0 g, 32.4 mmol) in toluene (50 ml). The mixture was stirred at room temperature for 1.5 h and heated at reflux for 3 h. The sol-vent was removed in vacuo and the residue was taken up in methanol (30 ml) and CH2Cl2 (30 ml) and stirred for 18 h. The mixture was evaporated in vacuo and the residue was taken up in EtOAc (50 ml), washed with saturated NaHCO3 solution (3×75 ml), dried and evaporated in vacuo to yield the title compound (4.5 g, 83%).

후처리

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. customThe sol-vent was removed in vacuo
  4. stirringCH2Cl2 (30 ml) and stirred for 18 h
  5. customThe mixture was evaporated in vacuo
  6. washwashed with saturated NaHCO3 solution (3×75 ml)
  7. customdried
  8. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-a92516418eb34081835e188e8b1ab188
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202858B2

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