Carbon tetrabromide → 4-Bromo-2-bromomethyl-7-methoxybenzofuran

HRID 1108318Notes

Reaction equation

HRID 1108318 reaction equation
[C:1]([Br:5])(Br)(Br)Br.[Br:6][C:7]1[C:12]2[CH:13]=[C:14](CO)[O:15][C:11]=2[C:10]([O:18][CH3:19])=[CH:9][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:6][C:7]1[C:12]2[CH:13]=[C:14]([CH2:1][Br:5])[O:15][C:11]=2[C:10]([O:18][CH3:19])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 18784868(4-Bromo-7-methoxybenzofuran-2-yl)-methanol

Product 1

HCID 187848624-Bromo-2-bromomethyl-7-methoxybenzofuranYield 62.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Carbon tetrabromide (1.52 g) was added to a stirred solution of (4-bromo-7-methoxybenzofuran-2-yl)-methanol (1 g) in dichloromethane (10 ml) at 0° C. under an inert atmosphere. Triphenylphosphine (1.53 g) was then added and the reaction stirred for 1 h. The reaction mixture was preadsorbed onto silica and purified by column chromatography eluting with 25% ethyl acetate in hexane to afford the title compound as a yellow solid (0.78 g).

Workup

  1. custompurified by column chromatography
  2. washeluting with 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e55d8e4de56b4819bfd6913dc5e6b8b7
Source dataset
uspto-grants-2000_05
Patent number
US06066657

Reaction notes

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