Diphenyl disulfide → HCID 20386680, compound

HRID 46647

Reaction equation

HRID 46647 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1.[C:16]1([S:22]Cl)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(SSC2C=CC=CC=2)C=CC=CC=1>[Fe].C(Cl)(Cl)(Cl)Cl>[C:16]1([S:22][C:11]2[S:10][C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:14])[F:15])[CH:4]=3)=[CH:13][CH:12]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 13436Diphenyl disulfideHCID 11008040Benzenesulfenyl chloride2×HCID 20100092HCID 20100092, compound2×

Product 1

HCID 20386680HCID 20386680, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 29.7 g (0.13 mole) of 2-(m-trifluoromethylphenyl)thiophene, 200 ml of reagent carbon tetrachloride, 15.5 ml (18.8 g 0.13 mole) of benzene sulfenyl chloride and 0.05 g of iron powder was allowed to stand 4 days at room temperature. The reaction mixture was found by vapor phase chromatography to contain approximately equal amounts of 2-(m-trifluoromethylphenyl)thiophene, diphenyl disulfide and the desired disubstituted thiophene. An additional 12.7 ml (0.11 mole) of benzenesulfenyl chloride and 0.05 g of iron powder were added. The mixture was stirred 2 hours at room temperature and then 1 hour at reflux. The carbon tetrachloride solvent was removed by distillation. The residue was distilled at reduced pressure to give 17 g (39%) of 2-phenylthio-5-(m-trifluoromethylphenyl)thiophene b.p. 172°-210° C. (0.04 mm), nD21 =1.6329-1.6330.

Workup

  1. temperature1 hour at reflux
  2. customThe carbon tetrachloride solvent was removed by distillation
  3. distillationThe residue was distilled at reduced pressure

Sources & evidence

ORD record
ord-9fe412f2328447858a41a74d2ca3d546
Source dataset
uspto-grants-1979_11
Patent number
US04174405

Linked notes

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