Methanol → Methyl 4-chloro-3-fluorobenzoate

HRID 1846972노트

반응식

HRID 1846972 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[F:11].S(Cl)(Cl)=O.[CH3:16]O>>[CH3:16][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([F:11])[CH:4]=1

참가 물질

4

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27365364-Chloro-3-fluorobenzoic acid

생성물 1

HCID 2780856Methyl 4-chloro-3-fluorobenzoate

실험 절차

A solution of 4-chloro-3-fluoro benzoic acid (450.0 g, 2.586 mol, Fluororochem, Derbyshire, UK) in methanol (4.5 L) was cooled to 0° C. and thionyl chloride (450.0 mL) was added over 30 minutes. The reaction mixture was stirred for 12 hours at ambient temperature. The reaction was monitored by TLC. Upon completion, the solvent was removed under reduced pressure and the residue was quenched with 1.0 M sodium bicarbonate solution (500 mL). The aqueous layer was extracted with dichloromethane (2×5.0 L). The combined organic layer was washed with brine (2.5 L), dried over anhydrous sodium sulfate and concentrated under reduced pressure afforded the title compound as light brown solid. The crude compound was used in the next step without further purification.

후처리

  1. customUpon completion, the solvent was removed under reduced pressure
  2. customthe residue was quenched with 1.0 M sodium bicarbonate solution (500 mL)
  3. extractionThe aqueous layer was extracted with dichloromethane (2×5.0 L)
  4. washThe combined organic layer was washed with brine (2.5 L)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2e24bd45f6d5472fa78149e606756173
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952036B2

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