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

HRID 82747Notes

Reaction equation

HRID 82747 reaction equation
[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]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 115633-Bromophenol

Product 1

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

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-e967a84eaca949648371400592c1fba9
Source dataset
uspto-grants-2014_09
Patent number
US08846736B2

Reaction notes

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