Acetyl chloride → Phenol, 3-bromo-, 1-acetate

HRID 82747

反応式

HRID 82747 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9](Cl)(=[O:11])[CH3:10]>N1C=CC=CC=1.ClCCl>[C:9]([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)(=[O:11])[CH3:10]

参加物

5

反応物 2

HCID 6367Acetyl chlorideHCID 115633-Bromophenol

生成物 1

HCID 141946Phenol, 3-bromo-, 1-acetate収率 74%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred suspension of 3-bromophenol (50 g, 0.29 mol) in pyridine (200 mL) and dichloromethane (100 mL) was added dropwise acetyl chloride (25 mL, 0.35 mol) at 0° C. and the mixture was stirred 18 h at room temperature. LC-MS showed that the reaction was complete. Pyridine and dichloromethane was evaporated in vacuo. Water (600 mL) was added and acidified with hydrochloric acid at pH 2. The reaction mixture was extracted with ethyl acetate (500 mL×3) and the organic phase was dried over anhydrous sodium sulfate, filtrated, concentrated and purified by column chromatography (PE:EA=60:1) to afford compound E-1 as a colorless liquid (46 g, 74%).

後処理

  1. customPyridine and dichloromethane was evaporated in vacuo
  2. additionWater (600 mL) was added
  3. extractionThe reaction mixture was extracted with ethyl acetate (500 mL×3)
  4. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated
  7. custompurified by column chromatography (PE:EA=60:1)

出典と根拠

ORDレコード
ord-e967a84eaca949648371400592c1fba9
出典データセット
uspto-grants-2014_09
特許番号
US08846736B2

関連ノート

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