Phosphorus tribromide → 5-(Bromomethyl)-2-methoxybenzonitrile
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6]O)#[N:2].P(Br)(Br)[Br:14]>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6][Br:14])#[N:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 3-cyano-4-methoxybenzyl alcohol (500 mg) in dichloromethane (5 mL) was added phosphorus tribromide (0.146 mL) under ice-water cooling. The mixture was stirred at 0° C. for 3 hours and partitioned between chloroform and water. The separated organic layer was washed successively with water, an aqueous saturated sodium bicarbonate solution and brine. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residual solid was triturated with diisopropyl ether to give 3-cyano-4-methoxybenzyl bromide as an off-white solid (456.3 mg).
Workup
- custompartitioned between chloroform and water
- washThe separated organic layer was washed successively with water
- dry with materialThe organic layer was dried over magnesium sulfate
- customevaporated in vacuo
- customThe residual solid was triturated with diisopropyl ether
Sources & evidence
- ORD record
- ord-e86e137fd44248c0a693a50727711c04
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06582351B1
Reaction notes
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