Hydrogen Bromide → 4-Methoxybenzyl bromide

HRID 484053Notes

Reaction equation

HRID 484053 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9]O)=[CH:7][CH:8]=1.[BrH:11]>CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][Br:11])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 77384-Methoxybenzyl alcohol

Product 1

HCID 1650214-Methoxybenzyl bromideYield 116.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

p-Methoxybenzyl alcohol (13.8 g, 0.1 mol) was added dropwise to a solution of 48% HBr (50 gm, 0.3 mol of HBr) over a period of 15 min and the solution was then stirred for an additional 15 min before being poured into a mixture of ice-H2O and Et2O. The layers were separated and the aqueous layer was extracted with Et2O. The combined Et2O extracts were washed with sat. NaCl, dried over Na2SO4 and evaporated to dryness to give 23.4 gm of p-methoxybenzyl bromide suitable for use in the next step.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with Et2O
  3. washThe combined Et2O extracts were washed with sat. NaCl
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-f4e7aaf0da4c4705a618dfaf2e837418
Source dataset
uspto-grants-1993_07
Patent number
US05229381

Reaction notes

Loading…