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

HRID 2096485Notes

Reaction equation

HRID 2096485 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1>C(Cl)Cl>[C:5]([O:16][C:13]1[CH:14]=[CH:15][C:10]([Br:9])=[CH:11][CH:12]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 78084-BromophenolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 74726Phenol, 4-bromo-, 1-acetateYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the suspension of anhydrous aluminum chloride (84.0 g, 0.49 mol) in methylene chloride (1200 mL) was add acetyl chloride (49.2 g, 0.63 mol) while stirring and cooling on ice. The mixture was stirred for 20 minutes while cooling on ice followed by addition of 4-bromophenol (98 g, 0.57 mol). The reaction mixture was stirred at room temperature for 1 h and then ice water was added. The reaction mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography to yield 4-bromophenyl acetate (104.0 g, 85%). 1H-NMR (CDCl3): 2.28 (s, 3 H), 6.98 (d, 2 H), 7.48 (d, 2 H).

Workup

  1. temperaturecooling on ice
  2. stirringThe mixture was stirred for 20 minutes
  3. temperaturewhile cooling on ice
  4. stirringThe reaction mixture was stirred at room temperature for 1 h
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationAfter distilling off the solvent under reduced pressure
  9. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9de00ee083364512a642829a1bb1fd85
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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