Water → 4-(Bromomethyl)-2-chloro-1-methoxybenzene

HRID 1370124Notes

Reaction equation

HRID 1370124 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5]O.P(Br)(Br)[Br:13].O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5][Br:13]

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 4312004(3-Chloro-4-methoxyphenyl)methanol

Product 1

HCID 114703704-(Bromomethyl)-2-chloro-1-methoxybenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloro-4-methoxybenzyl alcohol (164 g) in dichloromethane (800 ml) was added phosphorus tribromide (45.1 ml) under ice-cooing and the mixture was stirred at ambient temperature for an hour followed by adding water to the mixture. The separated aqueous layer was extracted with dichloromethane. The combined organic layers were washed with an aqueous saturated sodium bicarbonate solution and brine, dried over magnesium sulfate, and evaporated in vacuo. The oily residue was triturated with n-hexane to obtain 3-chloro-4-methoxybenzyl bromide (200 g) as a white powder.

Workup

  1. extractionThe separated aqueous layer was extracted with dichloromethane
  2. washThe combined organic layers were washed with an aqueous saturated sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe oily residue was triturated with n-hexane

Sources & evidence

ORD record
ord-ed23a854858647ca82ce7ee9523f5d99
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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