Sodium Hydroxide → 2-(3-Bromo-4-formyl-phenoxy)-4-trifluoromethyl-benzonitrile

HRID 1178534Notes

Reaction equation

HRID 1178534 reaction equation
F[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Br:14][C:15]1[CH:22]=[C:21]([OH:23])[CH:20]=[CH:19][C:16]=1[CH:17]=[O:18].[F-].[K+].[OH-].[Na+]>CN(C=O)C>[Br:14][C:15]1[CH:22]=[C:21]([CH:20]=[CH:19][C:16]=1[CH:17]=[O:18])[O:23][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 5189732-Fluoro-4-(trifluoromethyl)benzonitrileHCID 522689Potassium FluorideHCID 110848662-Bromo-4-hydroxybenzaldehyde

Product 1

HCID 219303412-(3-Bromo-4-formyl-phenoxy)-4-trifluoromethyl-benzonitrileYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Fluoro-4-trifluoromethyl-benzonitrile (3.1 g, 20 mmol), 2-bromo-4-hydroxybenzaldehyde (4 g, 20 mmol) and potassium fluoride (3.47 g, 60 mmol) were heated with stirring in dry DMF (20 mL) at 120° C. for 4 h, 80° C. for 16 h, 120° C. for 4 h, 130° C. for 1 h, and then at 140° C. for 16 h. The reaction mixture was cooled, poured onto 1N sodium hydroxide, extracted with ethyl acetate, and then dried over MgSO4. After filtration, the solvent was removed in vacuo to yield 2-(3-bromo-4-formyl-phenoxy)-4-trifluoromethyl-benzonitrile (6.38 g, 96%) as a brown oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-30821c9e7cfd4bd7a803a1bc950d21e8
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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