Phenacyl bromide → 3Phenacyloxy-5-trifluoromethylbenzoic Acid

HRID 1606757Notes

Reaction equation

HRID 1606757 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[H-].[Na+].[H][H].Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:22]>CS(C)=O>[CH2:20]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1)[C:5]([OH:7])=[O:6])[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:22]

Participants

6

Reactant 4

HCID 6259Phenacyl bromideHCID 24758Sodium hydrideHCID 27831463-hydroxy-5-(trifluoromethyl)benzoic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 215445003Phenacyloxy-5-trifluoromethylbenzoic Acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 206 mg. (1 m mole) of 3-hydroxy-5-trifluoromethylbenzoic acid dissolved in 2.5 ml. of dimethylsulfoxide is added 85 mg. (2 m moles) of a 56.6% sodium hydride suspension in oil. When the hydrogen evolution has ceased, 199 mg. (1 m mole) of α-bromoacetophenone is added and the reaction mixture is allowed to stir at room temperature for 2 hours. The reaction is diluted with 10 ml. of water and extracted with ether. The aqueous phase is acidified and the product extracted with ether. Removal of the ether under reduced pressure followed by sublimation at 150° C. and 0.1 mm pressure provided the pure product, m.p. 180°-182° C.

Workup

  1. additionThe reaction is diluted with 10 ml
  2. extractionof water and extracted with ether
  3. extractionthe product extracted with ether
  4. customRemoval of the ether under reduced pressure
  5. customfollowed by sublimation at 150° C.
  6. custom0.1 mm pressure provided the pure product, m.p. 180°-182° C.

Sources & evidence

ORD record
ord-f6fecc6547244f4e9d5c4e238ad80653
Source dataset
uspto-grants-1976_04
Patent number
US03953595

Reaction notes

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