(2-Methylsulfanylphenyl)methanol → 1-(Bromomethyl)-2-(methylsulfanyl)benzene

HRID 1290013Notes

Reaction equation

HRID 1290013 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]O.[Br-:11].[Br-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CO>[CH3:1][S:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][Br:11]

Participants

4

Reactant 2

HCID 3551404(2-Methylsulfanylphenyl)methanolHCID 12890784Triphenylphosphane dibromide

Product 1

HCID 217935191-(Bromomethyl)-2-(methylsulfanyl)benzeneYield 51.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 400 mg (2.59 mmol) of 2-methylthio-benzylalcohol in 8 mL of methanol was added 1.42 g (3.37 mmol) of triphenylphosphine dibromide and stirred at room temperature for 18 h. The mixture was concentrated and purified by silica gel flash chromatography, eluting with 2% ethyl acetate/hexane to give 289 mg of the title compound. NMR (CDCl3): δ 2.50 (s, 3H), 4.63 (s, 2H), 7.13 (m, 1H), 7.27 (m, 2H), 7.34 (d, 1).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by silica gel flash chromatography
  3. washeluting with 2% ethyl acetate/hexane

Sources & evidence

ORD record
ord-453d8481790c4a13b55496e65d3ffb87
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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