Thiophenol → 2-Methyl-1-nitro-4-(phenylsulfanyl)benzene

HRID 1577147Notes

Reaction equation

HRID 1577147 reaction equation
[H-].[Na+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[C:11]1[CH:12]=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[C:15]([CH3:17])[CH:16]=1>CN(C)C=O>[N+:18]([C:14]1[CH:13]=[CH:12][C:11]([S:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[CH:16][C:15]=1[CH3:17])([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 815772-Bromo-5-nitrotoluene

Product 1

HCID 127696732-Methyl-1-nitro-4-(phenylsulfanyl)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (57% oil emulsion, 1.11 g) in dimethylformamide (30 ml) is added in small portions 2.48 ml (2.64 g, 24 mmoles) of thiophenol. The mixture is cooled in an ice bath while a solution of 5-bromo-2-nitrotoluene (4.32 g, 20 mmoles) in dimethylformamide (10 ml) is added dropwise. The mixture is stirred for an additional 30 minutes and then poured into ice water (200 ml). The partially crystalline product is extracted with dichloromethane and the combined extracts are washed with water and dried. The solvents are evaporated under high vacuum to remove DMF and the residue is covered with hexane. The resultant crystals are broken up and filtered to give pure product, 2-nitro-5-phenylthiotoluene, 3.78 g, m.p. 69°-75°.

Workup

  1. additionis added dropwise
  2. extractionThe partially crystalline product is extracted with dichloromethane
  3. washthe combined extracts are washed with water
  4. customdried
  5. customThe solvents are evaporated under high vacuum
  6. customto remove DMF
  7. filtrationfiltered

Sources & evidence

ORD record
ord-75a3a1b9d3114d60987e25a64118cfe8
Source dataset
uspto-grants-1981_09
Patent number
US04287201

Reaction notes

Loading…