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

HRID 1293121Notes

Reaction equation

HRID 1293121 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-440ae632023349a787dbf1966862a8ef
Source dataset
uspto-grants-2007_07
Patent number
US07238717B2

Reaction notes

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