4-Methoxybenzyl alcohol → 4-Methoxybenzyl bromide

HRID 1291175Notes

Reaction equation

HRID 1291175 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9]O)=[CH:7][CH:8]=1.C(Br)(Br)(Br)[Br:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][Br:12])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 77384-Methoxybenzyl alcoholHCID 11205Carbon tetrabromideHCID 11776Triphenylphosphine

Product 1

HCID 1650214-Methoxybenzyl bromideYield 47%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3.0 g (0.0217 mol) of p-methoxybenzyl alcohol were dissolved in 50 ml of ether and treated with 14.4 g (0.0433 mol) of carbon tetrabromide. 11.4 g (0.0433 mol) of triphenyl-phosphine were added while cooling with ice. The mixture was stirred at room temperature for 3 hrs. After removal of the solvent the residue was filtered over a short silica gel column with ether/hexane (1:1) as the eluent. The filtrate was subjected to a bulb-tube distillation. 2.05 g (47%) of 4-methoxybenzyl bromide were obtained as a colorless oil; b.p. 120°-140°(22 Torr). MS: me/e (% basic peak)=202, 200 (C8H9BrO+, 3), 121 (C8 H9O+, 100).

Workup

  1. temperaturewhile cooling with ice
  2. customAfter removal of the solvent the residue
  3. filtrationwas filtered over a short silica gel column with ether/hexane (1:1) as the eluent
  4. customThe filtrate was subjected to a bulb-tube
  5. distillationdistillation

Sources & evidence

ORD record
ord-c7f9db74b2d64968be4200570dbc59e9
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

Loading…