1-Chloro-4-nitrobenzene → 1-Fluoro-4-[(4-nitrophenyl)sulfanyl]benzene

HRID 510149Notes

Reaction equation

HRID 510149 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.Cl[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 11430Potassium CarbonateHCID 677894-Fluorothiophenol

Product 1

HCID 27830591-Fluoro-4-[(4-nitrophenyl)sulfanyl]benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-fluorobenzenethiol (9.86 g, 77 mmol), 1-chloro-4-nitrobenzene (12.72 g, 81 mmol) and potassium carbonate (21.25 g, 154 mmol) in acetonitrile (300 mL) is stirred at room temperature under inert atmosphere for 48 h. The mixture is diluted with water (750 mL) and the aqueous phase is extracted with dichloromethane (2×500 mL). The combined organic layers are dried over sodium sulphate, filtered and concentrated under reduced pressure. The desired product is isolated in the presence of some impurities as a yellow solid (19.4 g, 78 mmol) (HPLC-MS Method 2: retention time: 2.132 min, m/z no mass signal).

Workup

  1. extractionthe aqueous phase is extracted with dichloromethane (2×500 mL)
  2. dry with materialThe combined organic layers are dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7a7dba39b4e34955998c320858f647ca
Source dataset
uspto-grants-2015_08
Patent number
US09096599B2

Reaction notes

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