N-bromobutanimide → 3-Bromo-5-(trifluoromethyl)benzaldehyde

HRID 2071091Notes

Reaction equation

HRID 2071091 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7].[Br:13]N1C(=O)CCC1=O>S(=O)(=O)(O)O.O>[Br:13][C:9]1[CH:8]=[C:5]([CH:4]=[C:3]([C:2]([F:11])([F:12])[F:1])[CH:10]=1)[CH:6]=[O:7]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 679903-(Trifluoromethyl)benzaldehyde

Product 1

HCID 161154383-Bromo-5-(trifluoromethyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

To 3-(trifluoromethyl)benzaldehyde (5 gm, 28.72 mmol) in sulfuric acid (13.5 ml) at 60° C., N-bromosuccinimide (6.13 g, 34.45 mmol) was added in 3 portions. After 2 h, the reaction mixture was cooled, diluted with cold water and filtered. Filter cake was washed with hexane. Volatiles were removed under reduced pressure and the crude residue of 3-bromo-5-(trifluoromethyl)benzaldehyde was carried to the next step without purification.

Workup

  1. temperaturethe reaction mixture was cooled
  2. filtrationfiltered
  3. filtrationFilter cake
  4. washwas washed with hexane
  5. customVolatiles were removed under reduced pressure
  6. customthe crude residue of 3-bromo-5-(trifluoromethyl)benzaldehyde was carried to the next step without purification

Sources & evidence

ORD record
ord-55c9f391e93e4656902f23e6732ff89a
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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