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

HRID 915918ノート

反応式

HRID 915918 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e8a9a9e944ad4f3183cb5fe249758d1d
出典データセット
uspto-grants-2007_09
特許番号
US07268128B2

反応ノート

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