N-bromobutanimide → 5-Bromo-2-hydroxy-3-(trifluoromethoxy)benzaldehyde

HRID 385141Notes

Reaction equation

HRID 385141 reaction equation
[OH:1][C:2]1[C:9]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Br:15]N1C(=O)CCC1=O>ClCCl>[Br:15][C:7]1[CH:8]=[C:9]([O:10][C:11]([F:12])([F:13])[F:14])[C:2]([OH:1])=[C:3]([CH:6]=1)[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 27792702-Hydroxy-3-(trifluoromethoxy)benzaldehyde

Product 1

HCID 27792795-Bromo-2-hydroxy-3-(trifluoromethoxy)benzaldehydeYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-hydroxy-3-trifluoromethoxybenzaldehyde (10.38 g) was dissolved in dichloromethane (100 mL), and N-bromosuccinimide (9.41 g) was added to the solution, and then the mixture was stirred at room temperature for 30 minutes. The solvent was distilled off under reduced pressure and water was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, 10% sodium thiosulfate and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (14.27 g) as a brown solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure and water
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with 1N hydrochloric acid, 10% sodium thiosulfate and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-79854c2cfc0244569810b1151a8142f4
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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