Chloro(diphenyl)silane → 2-Benzyl-5,6-dibromo-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene

HRID 1013364

Reaktionsgleichung

[CH2:1]([N:8]1[CH2:15][CH:14]2[CH:10]([CH:11](O)[C:12]3[C:18]([Br:19])=[C:17]([Br:20])[S:16][C:13]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[SiH](C1C=CC=CC=1)C1C=CC=CC=1.C([O-])(O)=O.[Na+]>ClC(Cl)C.CCOC(C)=O>[CH2:1]([N:8]1[CH2:15][CH:14]2[CH:10]([CH2:11][C:12]3[C:18]([Br:19])=[C:17]([Br:20])[S:16][C:13]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

The product from step f) (300 mg, 0.69 mmol) in dichloroethane (2.6 ml) was treated with InCl3 (153 mg, 0.69 mmol) and chlorodiphenylsilane (457 mg, 2.08 mmol). The contents were heated to 60° C. for 16 hours. The reaction mixture was cooled to 22° C., poured into sat. NaHCO3 and diluted with EtOAc (75 ml); producing a white emulsion. The emulsion was passed through celite and the organic layer was separated, washed with brine (25 ml) and dried (MgSO4). The crude product was dissolved in 7:3 hexanes:EtOAc and passed through a plug of silica gel to give the subtitle compound. MS calculated for C16H15Br2NS+H 414, observed 412, 414, 416.

Aufarbeitung

temperatureThe reaction mixture was cooled to 22° C.
customproducing a white emulsion
customthe organic layer was separated
washwashed with brine (25 ml)
dry with materialdried (MgSO4)
dissolutionThe crude product was dissolved in 7:3 hexanes

Quellen und Nachweise

ORD-Eintrag: ord-d93270e23f514652841b6f02b2a5de08
Quelldatensatz: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07981919B2

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