Carbon tetrabromide → 4-(Methylthio)benzyl bromide

HRID 1934711Notes

Reaction equation

HRID 1934711 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]O)=[CH:5][CH:4]=1.C(Br)(Br)(Br)[Br:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Br:12])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 592968[4-(Methylsulfanyl)phenyl]methanol

Product 1

HCID 113679304-(Methylthio)benzyl bromideYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(methylthio)benzyl alcohol (2.00 g) and carbon tetrabromide (6.45 g) in dichloromethane (40 mL) was added triphenylphosphine (4.08 g), and the mixture was stirred for an hour at ambient temperature. After evaporation of the solvent, the residue was purified by a silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (20:1) to give 4-(methylthio)benzyl bromide (2.00 g) as a colorless oil.

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was purified by a silica gel column chromatography
  3. washeluting with a mixture of hexane and ethyl acetate (20:1)

Sources & evidence

ORD record
ord-d037758a649d401582a29bbd29c2e88f
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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