p-Fluoronitrobenzene → 7W-0016

HRID 1404683Notes

Reaction equation

HRID 1404683 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][SH:19].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O.O>CN(C=O)C>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][S:19][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 5807592-Chlorobenzyl mercaptanHCID 22728543Water ethylacetate

Product 1

HCID 14855757W-0016Yield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-fluoro-4-nitrobenzene (1.0 equivalent) and (2-chlorophenyl)methanethiol (1.0 equivalent) in DMF (1.0 M) at rt was added K2CO3 (2.0 equivalents). After 16 h, the rxn was transferred to EtOAc:water (1:1). The organic layer was separated and sequentially washed with water (2×) and brine. The material was dried (MgSO4), filtered and concentrated to afford (2-chlorobenzyl)(4-nitrophenyl)sulfane in 98% yield. The material was taken through without further purification.

Workup

  1. customThe organic layer was separated
  2. washsequentially washed with water (2×) and brine
  3. dry with materialThe material was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e4c386f426d6471b8e76e81512656e77
Source dataset
uspto-grants-2014_12
Patent number
US08912336B2

Reaction notes

Loading…