Benzyl Bromide → HCID 70556754, compound

HRID 1503872Notes

Reaction equation

HRID 1503872 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH2:9])=[C:4]([F:10])[CH:3]=1.Br[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:12]([N:9]([CH2:8][C:7]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([Br:1])=[CH:3][C:4]=1[F:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 70180404-Bromo-2-fluoro-5-methylaniline

Product 1

HCID 70556754HCID 70556754, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 4-bromo-2-fluoro-5-methylbenzenamine (1 g, 4.9 mmol), (bromomethyl)benzene (2.5 g, 14.7 mmol) and potassium carbonate (2 g, 14.7 mmol) in acetonitrile (80 mL) was heated in a sealed tube at 100° C. for 16 hours. After concentration, the residue was diluted with ethyl acetate (80 mL), washed with water (20 mL), dried over anhydrous sodium sulfate filtered, and concentrated. The residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 50/1 petroleum ether/ethyl acetate to give the title compound. MS: 384 (M+H+).

Workup

  1. concentrationAfter concentration
  2. additionthe residue was diluted with ethyl acetate (80 mL)
  3. washwashed with water (20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel (200-300 mesh)
  8. washeluting with 50/1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-473f6e55404d405da3f5c6773322c35c
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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