Dimethylformamide → Methyl 4-bromo-2-(difluoromethoxy)benzoate

HRID 915918

반응식

HRID 915918 반응식
CN(C)C=O.[Br:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([OH:17])[CH:8]=1.Cl[C:19]([F:25])([F:24])C(OC)=O.C(=O)([O-])[O-].[K+].[K+]>O>[Br:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([O:17][CH:19]([F:25])[F:24])[CH:8]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 73935Methyl chlorodifluoroacetateHCID 13983552Methyl 4-bromo-2-hydroxybenzoate

생성물 1

HCID 58959352Methyl 4-bromo-2-(difluoromethoxy)benzoate수율 23%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

To a 70 ml dimethylformamide solution of 5.0 g (21.7 mmol) of methyl 4-bromo-2-hydroxybenzoate, 3.4 ml (32.6 mmol) of methyl chlorodifluoroacetate and 3.0 g (21.7 mmol) of potassium carbonate were added. The mixture was stirred at 60° C. for 6 hours and at room temperature for 60 hours. Then, water was added to the reaction mixture, and the mixture was extracted with ether. The organic layer was washed with water and a saturated aqueous solution of sodium chloride. The washed system was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=8/1) to obtain 1.4 g (23%) of the captioned compound.

후처리

  1. extractionthe mixture was extracted with ether
  2. washThe organic layer was washed with water
  3. dry with materialThe washed system was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=8/1)

출처 및 근거

ORD 기록
ord-e8a9a9e944ad4f3183cb5fe249758d1d
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268128B2

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