Water → 4-(4-Bromo-3-methylphenylamino)benzonitrile

HRID 1260170Notes

Reaction equation

HRID 1260170 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[Br:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][C:12]=1[CH3:18].C(OC(C)(C)C)(C)(C)C.[K].O>CN(C)C=O>[Br:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[CH:13][C:12]=1[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 145174-FluorobenzonitrileHCID 233594-Bromo-3-methylanilineHCID 86607002Potassium tert-butyloxide

Product 1

HCID 292913054-(4-Bromo-3-methylphenylamino)benzonitrileYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-fluorobenzonitrile (12.61 g, 104 mmol) and 4-bromo-3-methylaniline (15.36 g, 82.56 mmol) in N,N-dimethylformamide (160 mL) on an ice water bath under a nitrogen balloon was added potassium tert-butyloxide (18.53 g, 165.12 mmol) portionwise. The reaction was stirred at room temperature overnight. Then water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure to get crude product. The crude was then recrystallized from ethyl acetate to give 4-(4-bromo-3-methylphenylamino)benzonitrile (5.675 g, 24%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customto get crude product
  6. customThe crude was then recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9a92cd0f7a0a4ad0a19a2c46477e265c
Source dataset
uspto-grants-2013_06
Patent number
US08470803B2

Reaction notes

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