Acetyl chloride → Phenol, 4-bromo-, 1-acetate

HRID 1976316Notes

Reaction equation

HRID 1976316 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:15](Cl)(=[O:17])[CH3:16]>C(#N)C>[C:15]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 78084-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 74726Phenol, 4-bromo-, 1-acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 10.0 g (57.8 mmol) of 4-bromophenol in 100 mL of acetonitrile was added 9.6 g (69.5 mmol) of potassium carbonate. A white slurry was obtained to which was added 8.6 mL (121.0 mmol) of acetyl chloride and the resultant reaction mixture was stirred at ambient temperature for 17.5 hours. The reaction mixture was filtered, washed with ethyl acetate and the filtrate was concentrated in vacuo to a yellow oil. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) gave the title compound as a clear, nearly colorless oil.

Workup

  1. customA white slurry was obtained to which
  2. customthe resultant reaction mixture
  3. filtrationThe reaction mixture was filtered
  4. washwashed with ethyl acetate
  5. concentrationthe filtrate was concentrated in vacuo to a yellow oil
  6. customPurification by flash chromatography (silica, 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-2957478e275a418fbe815edb492b30d7
Source dataset
uspto-grants-2001_05
Patent number
US06225494B1

Reaction notes

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