Acetic Anhydride → 4-Bromo-3,5-dimethylphenyl acetate

HRID 416161Notes

Reaction equation

HRID 416161 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[C:11](OC(=O)C)(=[O:13])[CH3:12]>N1C=CC=CC=1.Cl>[C:11]([O:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([Br:1])=[C:3]([CH3:10])[CH:4]=1)(=[O:13])[CH3:12]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 819704-Bromo-3,5-dimethylphenol

Product 1

HCID 151846854-Bromo-3,5-dimethylphenyl acetateYield 128.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-bromo-3,5-dimethylphenol (10.1 g, 50.0 mmol) in pyridine (13 mL) was added acetic anhydride (7.66 g, 38.6 mmol), and the mixture was stirred at 50° C. for 30 min. The reaction mixture was ice-cooled, diluted with 0.5 M hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (12.1 g, yield 99%) as a yellow oil.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d027c36679a43368401bcb0fe18b82e
Source dataset
uspto-grants-2012_01
Patent number
US08088821B2

Reaction notes

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