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

HRID 2046693Notes

Reaction equation

HRID 2046693 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-33a13f6abfbc45cab92779b9fbd58161
Source dataset
uspto-grants-2013_11
Patent number
US08592444B2

Reaction notes

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