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

HRID 1043097Notes

Reaction equation

HRID 1043097 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-ebb48609c819406090fe9802aa4af027
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

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