Benzyl Bromide → 4-Dibenzylamino-3-trifluoromethyl-benzonitrile

HRID 1777715Notes

Reaction equation

HRID 1777715 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[H-].[Na+]>CN(C=O)C>[CH2:14]([N:1]([CH2:10][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1)[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][C:3]=1[C:10]([F:11])([F:12])[F:13])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 27794884-Amino-3-(trifluoromethyl)benzonitrile

Product 1

HCID 674630994-Dibenzylamino-3-trifluoromethyl-benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-5-cyanobenzotrifluoride (1.0 g, 5.37 mmol, 1 eq) and benzyl bromide (2.55 mL, 21.5 mmol, 4.0 eq) in dry DMF (10 mL) was added at rt NaH (970 mg, 21.5 mmol, 4 eq) portion-wise under Ar(g). The reaction mixture was stirred at rt overnight, and was then partitioned with H2O (30 mL) and extracted with EtOAc (5×20 mL) and CH2Cl2 (20 mL). The combined organic extracts were dried over MgSO4 and the solvent was removed in vacuo. The residue was further purified by silica gel column chromatography with hexane/EtOAc (1:0-9:1) to yield the product, 2, as a pale yellow solid (1.66 g, 85%).

Workup

  1. customwas then partitioned with H2O (30 mL)
  2. extractionextracted with EtOAc (5×20 mL) and CH2Cl2 (20 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. customthe solvent was removed in vacuo
  5. customThe residue was further purified by silica gel column chromatography with hexane/EtOAc (1:0-9:1)
  6. customto yield the product, 2

Sources & evidence

ORD record
ord-0e45e4160de74b03aada985b41b3977e
Source dataset
uspto-grants-2016_02
Patent number
US09266879B2

Reaction notes

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