Benzene, 1-methyl-3-(methylthio)- → (4-Bromo-3-methylphenyl)(methyl)sulfane

HRID 423696Notes

Reaction equation

HRID 423696 reaction equation
[Br:1]Br.[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][CH3:11])[CH:5]=1>C(O)(=O)C>[Br:1][C:9]1[CH:8]=[CH:7][C:6]([S:10][CH3:11])=[CH:5][C:4]=1[CH3:3]

Participants

4

Reactant 2

HCID 21005Benzene, 1-methyl-3-(methylthio)-HCID 24408Bromine

Product 1

HCID 26370189(4-Bromo-3-methylphenyl)(methyl)sulfaneYield 82.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (2.52 mL, 48.9 mmol) was added dropwise to a solution of 1-methyl-3-(methylthio)benzene (6.14 g, 44.4 mmol) in acetic acid (150 mL) at 0° C. The reaction was then stirred at ambient temperature for 2 h. The reaction was concentrated, and the resulting crude product was purified by chromatography on a silica gel column using 0 to 10% EtOAc/hexane to give 7.94 g (82%) of 1-bromo-2-methyl-4-(methylthio)benzene as a clear oil. 1H NMR (400 MHz, DMSO-d6): δ 7.40 (d, 1H, J=8.3 Hz), 7.10 (d, 1H, J=2.1 Hz), 6.92 (dd, 1H, Ja=8.3 Hz, Jb=2.2 Hz), 2.45 (s, 3H), 2.35 (s, 3H); LRMS (ESI), m/z 218 (M+H).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe resulting crude product was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-8f3266c46d4c4cc69a715958e1f68090
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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