Carbon tetrabromide → 2-Methoxyphenethyl bromide

HRID 1370115Notes

Reaction equation

HRID 1370115 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[CH2:5][CH2:6]O.C(Br)(Br)(Br)[Br:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[CH2:5][CH2:6][Br:13]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 819092-Methoxyphenethyl alcohol

Product 1

HCID 5781992-Methoxyphenethyl bromideYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-methoxyphenethyl alcohol (500 mg) and carbon tetrabromide (1.53 g) in anhydrous dichloromethane (10 mL) was stirred at 0° C. under a nitrogen atmosphere. After adding triphenylphosphine (1.03 g) portionwise, the reaction mixture was stirred for an hour under the same condition. The reaction mixture was evaporated in vacuo and the residue was subjected to a silica gel column chromatography eluting with n-hexane only and then a mixture of n-hexane and ethyl acetate (40:1 to 20:1) to give 2-methoxyphenethyl bromide (661 mg) as an oil.

Workup

  1. stirringthe reaction mixture was stirred for an hour under the same condition
  2. customThe reaction mixture was evaporated in vacuo
  3. washeluting with n-hexane only
  4. additiona mixture of n-hexane and ethyl acetate (40:1 to 20:1)

Sources & evidence

ORD record
ord-3c6b7c184f2446658afad0c863a096b9
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

Loading…