Dimethylformamide → 2,3-Dichloro-4-(p-nitrophenylsulfenyl)anisole

HRID 2166847Notes

Reaction equation

HRID 2166847 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[SH:11].F[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[Cl:8][C:7]1[C:2]([Cl:1])=[C:3]([S:11][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[CH:4]=[CH:5][C:6]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 159142692,3-Dichloro-4-methoxybenzene-1-thiol

Product 1

HCID 131456822,3-Dichloro-4-(p-nitrophenylsulfenyl)anisole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,3-dichloro-4-methoxybenzenethiol (6.0 g., 0.024 mole), p-fluoronitrobenzene (3.04 ml., 0.029 mole) and anhydrous potassium carbonate (5.15 g., 0.038 mole) in 60 ml. of DMF was stirred at room temperature for 2 hours and then poured into water. The resulting solid product was filtered and washed well with ethanol to give 9.1 g. (96%), m.p. 236°-237°.

Workup

  1. filtrationThe resulting solid product was filtered
  2. washwashed well with ethanol
  3. customto give 9.1 g

Sources & evidence

ORD record
ord-8f41d96605b049c698fc4f7ffce2e032
Source dataset
uspto-grants-1983_06
Patent number
US04389416

Reaction notes

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