Water → 2-Bromo-5'-chloro-2'-hydroxyacetophenone

HRID 644460Notes

Reaction equation

HRID 644460 reaction equation
[Br-:1].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[Cl:34][C:35]1[CH:36]=[CH:37][C:38]([OH:44])=[C:39]([C:41](=[O:43])[CH3:42])[CH:40]=1.O>O1CCCC1>[Br:1][CH2:42][C:41]([C:39]1[CH:40]=[C:35]([Cl:34])[CH:36]=[CH:37][C:38]=1[OH:44])=[O:43]

Participants

5

Reactant 3

HCID 962WaterHCID 740613-Chloro-6-hydroxyacetophenoneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 27568852-Bromo-5'-chloro-2'-hydroxyacetophenoneYield 75.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyltrimethylammonium tribromide (0.44 g, 1.17 mmol) was added to a solution of 5′-chloro-2′-hydroxyacetophenone (0.20 g, 1.17 mmol) in tetrahydrofuran (6 mL) and the mixture was stirred at room temperature for 8 hours. The reaction mixture was poured into water and extracted with ethyl acetate. After the ethyl acetate layer was washed with brine and dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1) to give the title compound (220.7 mg, 75.6%) as an yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the ethyl acetate layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe residue obtained by evaporation of the solvent under reduced pressure
  5. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-79b32115f5f04216a017deb8b75c8c1a
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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