Benzyl Bromide → N,N-dibenzyl-4-bromo-2-(trifluoromethoxy)aniline

HRID 1503862Notes

Reaction equation

HRID 1503862 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][C:10]([F:13])([F:12])[F:11])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C>[CH2:21]([N:6]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:5]1[CH:7]=[CH:8][C:2]([Br:1])=[CH:3][C:4]=1[O:9][C:10]([F:11])([F:12])[F:13])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 7373824-Bromo-2-(trifluoromethoxy)aniline

Product 1

HCID 70558473N,N-dibenzyl-4-bromo-2-(trifluoromethoxy)aniline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 4-bromo-2-(trifluoromethoxy)aniline (5 g, 19.53 mmol) and potassium carbonate (8.09 g, 58.89 mmol) in acetonitrile (200 mL) was added (bromomethyl)benzene (6.96 mL, 58.59 mmol) and the mixture was refluxed for 20 hours. The mixture was filtered and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 5/1 petroleum ether/ethyl acetate to give the title compound. MS: 436 (M+H+)

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by flash chromatography on silica gel (200-300 mesh)
  5. washeluting with 5/1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-25f509ad56d44b228a5efc8fafadd490
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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