Phosphorus tribromide → 1-(Bromomethyl)-2,3-dichlorobenzene

HRID 510432Notes

Reaction equation

HRID 510432 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9]O.[Br:11]P(Br)Br>C1(C)C=CC=CC=1>[Br:11][CH2:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 2286032,3-Dichlorobenzyl alcohol

Product 1

HCID 27346021-(Bromomethyl)-2,3-dichlorobenzeneYield 233.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (2,3-dichlorophenyl)methanol (75 g, 0.431 mol), in toluene (800 mL), tribromophosphine (40.7 g, 0.151 mol) was added dropwise at room temperature with stirring. Then the reaction mixture was stirred at room temperature for 2 h and concentrated. The resulting residue was neutralized with aq. NaHCO3 and extracted with DCM (300 mL*3). The organic layer was washed with brine, dried over Na2SO4, filtered and the filtrate was concentrated to provide the titled compound (84.7 g, 83%), as a deep red solid.

Workup

  1. stirringThen the reaction mixture was stirred at room temperature for 2 h
  2. concentrationconcentrated
  3. extractionextracted with DCM (300 mL*3)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e48f5f36a4ef4f608eefac9d6c4f6b53
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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