Triphenylsilanethiol → (2,4-Difluoro-5-nitrophenethylthio)triphenylsilane

HRID 407963Notes

Reaction equation

HRID 407963 reaction equation
[C:1]1([Si:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[SH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:21][C:22]1[CH:27]=[C:26]([F:28])[C:25]([CH:29]=[CH2:30])=[CH:24][C:23]=1[N+:31]([O-:33])=[O:32].N(/C(C)(C)C#N)=N\C(C)(C)C#N>C1C=CC=CC=1>[F:28][C:26]1[CH:27]=[C:22]([F:21])[C:23]([N+:31]([O-:33])=[O:32])=[CH:24][C:25]=1[CH2:29][CH2:30][S:8][Si:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 621128TriphenylsilanethiolHCID 158566831,5-Difluoro-2-nitro-4-vinylbenzeneHCID 178449902HCID 178449902, compound

Product 1

HCID 15856684(2,4-Difluoro-5-nitrophenethylthio)triphenylsilaneYield 100%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A flask was charged with triphenylsilanethiol (12 g, 41 mmol), and 1,5-difluoro-2-nitro-4-vinylbenzene (5 g, 27 mmol) in benzene (80 mL), and then (E)-2,2′-(diazene-1,2-diyl)bis(2-methylpropanenitrile) (1.3 g, 8.1 mmol) was added. The mixture was refluxed for 1 hour, then cooled to ambient temperature and concentrated. The residue was purified using silica gel column chromatography with 10% acetone in hexanes to provide (2,4-difluoro-5-nitrophenethylthio)triphenylsilane (13 g, 27 mmol, 100% yield).

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. concentrationconcentrated
  3. customThe residue was purified

Sources & evidence

ORD record
ord-b9cd396ab60c48c7b3a231bdae984670
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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