Water → 4-Chloro-1-nitro-2-(phenylsulfanyl)benzene

HRID 1673062Notes

Reaction equation

HRID 1673062 reaction equation
F[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C(N(CC)CC)C.O.[C:20]1([SH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([S:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 8471TriethylamineHCID 696914-Chloro-2-fluoro-1-nitrobenzene

Product 1

HCID 147651164-Chloro-1-nitro-2-(phenylsulfanyl)benzeneYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2 g of 2-fluoro-4-chloro-nitrobenzene in 50 ml DMF and 1.25 ml of thiophenol was added 1.9 ml triethylamine at room temperature. The mixture was stirred for one hour. One hundred mL of water was added and a yellow solid crashed out of solution. The solid was collected by filtration and dried. Yield: 50-70%. LC-MS showed a single peak with the expected (M+H+) of 267.

Workup

  1. filtrationThe solid was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-379f40cb1263499f9f00b8b94e5eda19
Source dataset
uspto-grants-2011_08
Patent number
US07999109B2

Reaction notes

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