Triethylamine → 1-Fluoro-2-[(trifluoromethyl)sulfanyl]benzene

HRID 1848844Notes

Reaction equation

HRID 1848844 reaction equation
[F:1][C:2](I)([F:4])[F:3].[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[SH:13].C(N(CC)CC)C>CN(C)C=O.O>[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13][C:2]([F:4])([F:3])[F:1]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 16843TrifluoroiodomethaneHCID 5202162-Fluorothiophenol

Product 1

HCID 470028801-Fluoro-2-[(trifluoromethyl)sulfanyl]benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl viologen hydrochloride (1.17 g) in N,N-dimethylformamide (80 mL) at 25° C. was saturated with trifluoromethyl iodide, treated with 2-fluorobenzenethiol (9.7 mL) and triethylamine (20 mL), stirred for 24 hours, diluted with water (240 mL) and extracted with diethyl ether. The extract was washed with 1M aqueous NaOH, saturated ammonium chloride and brine and concentrated.

Workup

  1. customat 25° C.
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with 1M aqueous NaOH, saturated ammonium chloride and brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-01ac158b0a75457f90ce47c647bf17b4
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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