Carbon tetrabromide → 1-(Bromomethyl)-2-methoxybenzene

HRID 1972552Notes

Reaction equation

HRID 1972552 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:31]>ClCCl>[Br:31][CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 691542-Methoxybenzyl alcohol

Product 1

HCID 403081-(Bromomethyl)-2-methoxybenzeneYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 100-mL round-bottomed flask was added 2-methoxybenzyl alcohol (1.33 mL, 9.99 mmol, Aldrich, St. Louis, Mo.), triphenylphosphine (2.62 g, 9.99 mmol, Aldrich, St. Louis, Mo.) and carbon tetrabromide (0.969 mL, 9.99 mmol, Aldrich, St. Louis, Mo.) in dichloromethane (20 mL). The reaction mixture was stirred at room temperature for 4 h and then the solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 10% EtOAc in hexanes to give 1-(bromomethyl)-2-methoxybenzene (1.78 g) as a white solid.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-5029d73fb0c34b32bb6e099fc823f583
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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