Reaktion #1341494

Reaktionsgleichung

4-bromobenzothiophene

chlorotrimethylsilane

LDA

THF heptane

→

4-bromo-2-(trimethylsilyl)benzothiophene

Lösungsmittel

ether

HCl

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe organic layer was separated
2. 2
   Waschenwashed with sat'd aq NaHCO3 (20 mL)
3. 3
   Trocknendried over MgSO4
4. 4
   SonstigeRemoval of the solvent
5. 5
   workup.WAITleft 4-bromo-2-(trimethylsilyl)benzothiophene (740 mg, 95%) as an amber oil

Vorschrift

A stirred solution of ˜80% pure 4-bromobenzothiophene (580 mg, 2.7 mmol) and chlorotrimethylsilane (0.70 mL, 5.4 mmol) in dry THF (10 mL) was cooled to −70° C. and 2 M LDA in 1:1 THF/heptane (1.35 mL, 5.4 mmol) was added dropwise over 2 min. The mixture was stirred at −70° C. for 1.5 h and diluted with ether (80 mL) and 5% aq HCl (20 mL). The organic layer was separated, washed with sat'd aq NaHCO3 (20 mL) and dried over MgSO4. Removal of the solvent left 4-bromo-2-(trimethylsilyl)benzothiophene (740 mg, 95%) as an amber oil.

Quelle