Phosphorus tribromide → Benzenemethanamine, 3-(bromomethyl)-4-chloro-N,N-diethyl-

HRID 577013Notes

Reaction equation

HRID 577013 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[CH:4][C:3]=1[CH2:14]O.P(Br)(Br)[Br:17]>ClCCl>[Br:17][CH2:14][C:3]1[CH:4]=[C:5]([CH2:8][N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 59589352HCID 59589352, compound

Product 1

HCID 66815196Benzenemethanamine, 3-(bromomethyl)-4-chloro-N,N-diethyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {2-chloro-5-[(diethylamino)methyl]phenyl}methanol (3.0 g, 13.2 mmol) in anhydrous dichloromethane (80 mL) was added dropwise phosphorus tribromide (2.5 mL, 26.4 mmol). The mixture was stirred at room temperature overnight. The solvent was evaporated. The residue was dried in vacuo, affording {[3-(bromomethyl)-4-chlorophenyl]methyl}diethylamine. The product was used without further purification.

Workup

  1. customThe solvent was evaporated
  2. customThe residue was dried in vacuo

Sources & evidence

ORD record
ord-d9abb775ec454232812831b90259a729
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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