Hydrochloric Acid → 1-(4-Bromo-2-hydroxyphenyl)ethan-1-one

HRID 518148Notes

Reaction equation

HRID 518148 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10].Cl.[Al+3].[Cl-].[Cl-].[Cl-]>N1C=CC=CC=1.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:9](=[O:11])[CH3:10])=[C:4]([OH:8])[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 115633-BromophenolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 107274031-(4-Bromo-2-hydroxyphenyl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1049PyridineSolvent

Procedure

3-Bromo-phenol (10.0 g, 57.8 mmol) was dissolved in 10 ml of pyridine and 10 ml of acetic anhydride and stirred overnight at RT. The mixture was then poured into water, and 1 M HCl was added until reaching a neutral pH value. Extraction with AcOEt furnished a crude product, which was treated with AlCl3 (13.25 g, 100 mmol) at 140° C. After 2 h, the mixture was poured into water and extracted with diethyl ether. The crude residue was purified by column chromatography (eluent: hexane/AcOEt 70:30) to give 1-(4-bromo-2-hydroxy-phenyl)-ethanone (10.1 g) as a red solid.

Workup

  1. additionwas added
  2. extractionExtraction with AcOEt
  3. customfurnished a crude product, which
  4. extractionextracted with diethyl ether
  5. customThe crude residue was purified by column chromatography (eluent: hexane/AcOEt 70:30)

Sources & evidence

ORD record
ord-1cc9f6f546d541ebbdcdf435208047a5
Source dataset
uspto-grants-2015_08
Patent number
US09115148B2

Reaction notes

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