1-(3-Fluoro-4-methoxyphenyl)ethan-1-one → 1-(3-Fluoro-4-hydroxyphenyl)ethan-1-one

HRID 2372249Notes

Reaction equation

HRID 2372249 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10]C)=[C:6]([F:12])[CH:5]=1)=[O:3].[Br-].[Al+3].[Br-].[Br-]>C1(C)C=CC=CC=1>[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([F:12])[CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 968281-(3-Fluoro-4-methoxyphenyl)ethan-1-oneHCID 166749Bromhydrol

Product 1

HCID 27373251-(3-Fluoro-4-hydroxyphenyl)ethan-1-oneYield 93.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 400 ml of dried toluene was added 20.4 g of 3-fluoro-4-methoxyacetophenone, which was uniformly stirred at room temperature and added with 66.1 g of anhydrous aluminum bromide over about 20 minutes. After the stirring at room temperature for 4 hours, the reaction mixture was poured into 600 ml of ice water. After the separation into two layers, the extraction with ether on aqueous layer was repeated two times, and then the organic layers were gathered, washed with water and dried on magnesium sulfate. After magnesium sulfate was filtered off, the filtrate was concentrated and dried under a reduced pressure to obtain 17.45 g of a brown crystal. This crystal was recrystallized with toluene to obtain 16.53 g (yield: 88%) of a white crystal having a melting point of 127.0°-128.2° C.

Workup

  1. customAfter the separation into two layers
  2. extractionthe extraction with ether on aqueous layer
  3. washwashed with water
  4. customdried on magnesium sulfate
  5. filtrationAfter magnesium sulfate was filtered off
  6. concentrationthe filtrate was concentrated
  7. customdried under a reduced pressure

Sources & evidence

ORD record
ord-61e6f37cf16f49beb7ae3c48f658bbd3
Source dataset
uspto-grants-1992_03
Patent number
US05098602

Reaction notes

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