Phosphorus tribromide → 1-Benzyloxy-2-bromomethyl-4-iodobenzene
Reaction equation
P(Br)(Br)[Br:2].[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([I:19])=[CH:15][C:14]=1[CH2:20]O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1(C)C=CC=CC=1>[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([I:19])=[CH:15][C:14]=1[CH2:20][Br:2])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
3.3 ml (35 mmol) of phosphorus tribromide are added dropwise to a solution of 35 g (103 mmol) of (2-benzyloxy-5-iodophenyl)methanol (Example 3A) in 350 ml of toluene at 40° C. The temperature of the reaction mixture is raised to 100° C. over the course of 15 min and the reaction mixture is stirred at this temperature for a further 10 min. After cooling, the two phases are separated. The organic phase is washed twice with distilled water and once with a saturated aqueous sodium chloride solution. The organic phase is dried over sodium sulfate and evaporated. The yield amounts to 41 g (99% of theory).
Workup
- temperatureAfter cooling
- customthe two phases are separated
- washThe organic phase is washed twice with distilled water and once with a saturated aqueous sodium chloride solution
- dry with materialThe organic phase is dried over sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-660b33039c7649dcb4e5d398f7ec064a
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07446102B2
Reaction notes
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