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

HRID 82747

반응식

HRID 82747 반응식
[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]

참가 물질

5

반응물 2

HCID 6367Acetyl chlorideHCID 115633-Bromophenol

생성물 1

HCID 141946Phenol, 3-bromo-, 1-acetate수율 74%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-e967a84eaca949648371400592c1fba9
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846736B2

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