Phosphorus tribromide → 1-(Benzyloxy)-2-(bromomethyl)-4-chlorobenzene
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:6]([CH2:8]O)[CH:7]=1.P(Br)(Br)[Br:19]>ClCCl>[C:12]1([CH2:11][O:10][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=2[CH2:8][Br:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
{5-chloro-2-[(phenylmethyl)oxy]phenyl}methanol (8.2 g, 33 mmol) was dissolved in dry dichloromethane under nitrogen and cooled to −10° C. Phosphorus tribromide (3.12 ml, 33 mmol) in dry dichloromethane (15 ml) was added slowly. The mixture was left at −10° C. for 15 mins, then stirred at room temperature overnight. TLC showed no more starting material. The mixture was then quenched with a saturated sodium hydrogen carbonate solution added very slowly. The mixture was diluted with dichloromethane and brine was added to aid separation. The organic phase was washed with water (×2), then dried (MgSO4) and evaporated. The residue was purified (50 g SPE column). Product comes off using 5% ethyl acetate in isohexane. White-ish solid obtained (8.1 g).
Workup
- customThe mixture was then quenched with a saturated sodium hydrogen carbonate solution
- additionadded very slowly
- additionThe mixture was diluted with dichloromethane and brine
- additionwas added
- customseparation
- washThe organic phase was washed with water (×2)
- dry with materialdried (MgSO4)
- customevaporated
- customThe residue was purified (50 g SPE column)
- customWhite-ish solid obtained (8.1 g)
Sources & evidence
- ORD record
- ord-424a12a17d614faca7636c1244816676
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07759369B2
Reaction notes
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