Dimethyl Sulfide → 4-Bromo-1-(methylthio)-2-(trifluoromethyl)-benzene

HRID 1694758Notes

Reaction equation

HRID 1694758 reaction equation
N(OCCC(C)C)=O.[Br:9][C:10]1[CH:16]=[CH:15][C:13](N)=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:11]=1.[CH3:21][S:22]C>C(#N)C>[Br:9][C:10]1[CH:16]=[CH:15][C:13]([S:22][CH3:21])=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:11]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 8053Isoamyl NitriteHCID 679604-Bromo-2-(trifluoromethyl)aniline

Product 1

HCID 223153184-Bromo-1-(methylthio)-2-(trifluoromethyl)-benzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Isopentyl nitrite (0.67 ml) was added dropwise to a solution of 4-bromo-2-(trifluoromethyl)aniline (1.2 g) and dimethyl sulfide (0.45 ml) in acetonitrile (12 ml). The reaction was slowly heated to reflux and then refluxed until gas evolution ceased. The volatiles were evaporated, the residue absorbed onto silica and the product eluted off with isohexane. Yield 0.8 g.

Workup

  1. temperatureThe reaction was slowly heated
  2. temperatureto reflux
  3. temperaturerefluxed until gas evolution
  4. customThe volatiles were evaporated
  5. customthe residue absorbed onto silica
  6. washthe product eluted off with isohexane

Sources & evidence

ORD record
ord-dc8b7ab79bc34bd084b3272e923b0fb5
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Reaction notes

Loading…