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

HRID 1408758Notes

Reaction equation

HRID 1408758 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>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:5](=[O:7])[CH3:6])=[CH:12][CH:11]=1

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

Anhydrous aluminum chloride (84 g, 0.486 mol) is suspended in methylene chloride (1200 mL), and then acetyl chloride (49.2 g, 0.629 mol) is added while stirring and cooling on ice. The mixture is stirred for 20 minutes while cooling on ice and 4-bromophenol (98 g, 0.57 mol) is added. The reaction mixture is stirred at room temperature for 1 h, and then ice water is added and extraction is performed with ethyl acetate. The organic layer is washed with brine and then dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue is purified by silica gel column chromatography to yield acetic acid 4-bromo-phenyl ester (104 g, 85%). 1H-NMR (CDCl3): 2.28 (s, 3H), 6.98 (d, 2H), 7.48 (d, 2H).

Workup

  1. temperaturecooling on ice
  2. stirringThe mixture is stirred for 20 minutes
  3. additionis added
  4. stirringThe reaction mixture is stirred at room temperature for 1 h
  5. extractionextraction
  6. washThe organic layer is washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationAfter distilling off the solvent under reduced pressure
  9. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2d62eb16d333472b9303cb163a8dec4a
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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