1,3-Difluoro-2-nitrobenzene → 305811-06-7

HRID 1816235Notes

Reaction equation

HRID 1816235 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][SH:13].[Na]>C(O)C>[CH3:12][S:13][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 879221,3-Difluoro-2-nitrobenzeneHCID 45051789Methylmercaptan sodium

Product 1

HCID 11052367305811-06-7Yield 84.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,6-Difluoronitrobenzene (1.0 g, 6.3 mmol) was stirred in ethanol (10 mL) and treated with sodium methylmercaptan (0.44 g, 6.3 mmol) in several portions over 5 minutes. After stirring for 2 hours the mixture was evaporated and chromatographed on silica gel (70% hexane:30% ethyl acetate) to give 2-methylmercapto-6-fluoronitrobenzene (approximately 1.0 g), which was reduced in ethanol (30 mL) using 5% palladium on carbon (0.3 g) and hydrogen (50 psi) for 2 hours. The catalyst was removed by filtration through celite and the solvent evaporated to give 2-fluoro-6-(methylthio)benzenamine (0.69 g).

Workup

  1. customwas evaporated
  2. customchromatographed on silica gel (70% hexane:30% ethyl acetate)

Sources & evidence

ORD record
ord-7fe8e2553b1940bf9925ee70ab9639a5
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

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