Benzyl Bromide → HCID 70558151, compound

HRID 1503818Notes

Reaction equation

HRID 1503818 reaction equation
[Br:1][C:2]1[C:8]([F:9])=[CH:7][C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(#N)C>[CH2:18]([N:6]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:5]1[CH:7]=[C:8]([F:9])[C:2]([Br:1])=[CH:3][C:4]=1[F:10])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27732854-Bromo-2,5-difluoroaniline

Product 1

HCID 70558151HCID 70558151, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 4-bromo-2,5-difluoroaniline (8 g, 39 mmol) and potassium carbonate (16 g, 116 mmol) in acetonitrile (200 mL) was added (bromomethyl)benzene (14.5 g, 85 mmol). After refluxing 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: 388 (M+H+).

Workup

  1. temperatureAfter refluxing 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-09edcdff4bbd4c9285c20fd7597328a0
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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