Hydrogen Bromide → 3-(Trifluoromethyl)phenylglyoxal

HRID 1881526Notes

Reaction equation

HRID 1881526 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1)=[O:3].Br.[OH2:15]>CS(C)=O>[O:3]=[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:5]=1)[CH:1]=[O:15]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 676823'-(Trifluoromethyl)acetophenone

Product 1

HCID 27832843-(Trifluoromethyl)phenylglyoxalYield 128%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

3-Trifluoromethylacetophenone (11.80 mmol, 2.22 g) was dissolved in dimethyl sulfoxide (13 mL), and 48% hydrobromic acid (5.4 mL) was gradually added at room temperature. After overnight stirring at 70° C., the reactor was cooled to room temperature. After addition of water, the reaction solution was extracted with chloroform, and the extract was dried and filtered, and the solvent was evaporated to give the desired product as a yellow liquid (3.04 g (crude), yield 128%).

Workup

  1. temperaturethe reactor was cooled to room temperature
  2. extractionthe reaction solution was extracted with chloroform
  3. customthe extract was dried
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-1ca3a5b2c73e44f78404f1582bd8b9a0
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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