Phosphorus tribromide → 1-(Bromomethyl)-3-chloro-2-methylbenzene
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
Product 1
Reagents, catalysts & solvents 1
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
- customThe solvent was removed
- customthe residue was partitioned between EtOAc and brine
- concentrationThe organic layer was concentrated
- 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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