Carbon tetrabromide → 2-(Bromomethyl)-1,4-dimethoxybenzene

HRID 1452408Notes

Reaction equation

HRID 1452408 reaction equation
[C:1]([Br:5])(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:25]([C:27]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:28]=1CO)[CH3:26]>C1COCC1>[CH3:26][O:25][C:27]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:28]=1[CH2:1][Br:5]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 1184952,5-Dimethoxybenzyl alcohol

Product 1

HCID 5920212-(Bromomethyl)-1,4-dimethoxybenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carbon tetrabromide (0.47 g, 1.25 mmol) and triphenylphosphine (0.47 g, 1.25 mmol) were added to a solution of 2,5-dimethoxylbenzylalcohol (0.2 g, 1.19 mmol) in THF (10 ml) at room temperature. The mixture was stirred for two hours to form a precipitate which the preciptate was filtered off. The filtrate was evaprated and the crude product was chromatographed (ethyl acetate and hexane 7:3). The desired compound was isolated as a white solid (0.25 g, 93%).

Workup

  1. customto form a precipitate which the preciptate
  2. filtrationwas filtered off
  3. customthe crude product was chromatographed (ethyl acetate and hexane 7:3)

Sources & evidence

ORD record
ord-1fffe26fbd3e49558759f5e776d03b0a
Source dataset
uspto-grants-1997_02
Patent number
US05606037

Reaction notes

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