Phosphorus tribromide → 1-(Bromomethyl)-3-chloro-2-methylbenzene

HRID 1958011Notes

Reaction equation

HRID 1958011 reaction equation
P(Br)(Br)[Br:2].[Cl:5][C:6]1[C:7]([CH3:14])=[C:8]([CH2:12]O)[CH:9]=[CH:10][CH:11]=1>C1(C)C=CC=CC=1>[Br:2][CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([Cl:5])[C:7]=1[CH3:14]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 13169022(3-Chloro-2-methylphenyl)methanol

Product 1

HCID 105130911-(Bromomethyl)-3-chloro-2-methylbenzeneYield 203.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of phosphorus tribromide (0.422 mL, 4.47 mmol) in Toluene (30 mL) was added (3-chloro-2-methylphenyl)methanol (2 g, 12.77 mmol). The reaction was stirred at RT overnight. The solvent was removed and the residue was partitioned between EtOAc and brine. The organic layer was concentrated and the residue was purified by biotage (5% EA/hexane) to give the product (2.0 g, 71%). 1H NMR (400 MHz, CDCl3) δppm 7.36 (m, 1H), 7.24 (m, 1H), 7.12 (m, 1H), 4.56 (s, 2H). 2.48 (s, 3H).

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between EtOAc and brine
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified by biotage (5% EA/hexane)

Sources & evidence

ORD record
ord-bb8c0663e90045979d612542183e75cd
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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