Carbon tetrabromide → 5-Bromo-2-(2-thienylmethoxy)benzyl bromide

HRID 1455968Notes

Reaction equation

HRID 1455968 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[C:6]([CH:9]=1)[CH2:7]O.C(Br)(Br)(Br)[Br:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[C:6]([CH:9]=1)[CH2:7][Br:18]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 289814405-Bromo-2-(2-thienylmethoxy)benzenemethanol

Product 1

HCID 221055055-Bromo-2-(2-thienylmethoxy)benzyl bromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-bromo-2-(2-thienylmethoxy)benzyl alcohol (0.53 g, 1.77 mmoles) in dichloromethane (12 ml) was cooled in an ice bath and treated with carbon tetrabromide (0.73 g, 2.2 mmol) polymer bound triphenylphosphine (0.65 g, 1.95 mmol) and stirred at ambient temperature for 42 hours. The reaction was filtered and evaporated. Chromatography (eluant: ethyl acetate/hexane) gave 5-bromo-2-(2-thienylmethoxy)benzyl bromide as a white solid (0.29, 45%).

Workup

  1. filtrationThe reaction was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-994f6e71f46847b498bd0647c996af81
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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