Reaktion #435352

Reaktionsgleichung

NBS

7-methylbenzo[b]thiophene

benzoyl peroxide

→

title compound

Ausbeute 38.6%

7-(Bromomethyl)benzo[b]thiophene

Ausbeute 38.6%

Lösungsmittel

CCl4

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux
2. 2
   Sonstigewhile irradiating with a 250 W lamp
3. 3
   workup.STIRRINGThe reaction mixture was stirred
4. 4
   Temperaturat reflux for 3 h
5. 5
   TemperaturThe solution was cooled
6. 6
   Filtrationfiltered
7. 7
   Sonstigethe solvent evaporated in vacuo

Vorschrift

To a solution of intermediate 137, 7-methylbenzo[b]thiophene (1.0 g, 6.5 mmol) in CCl4 (20 mL) was added benzoyl peroxide (1.1 g, 4.54 mmol) followed by portionwise addition of NBS (1.15 g, 6.5 mmol). The reaction mixture stirred at reflux while irradiating with a 250 W lamp. The reaction mixture was stirred at reflux for 3 h. The solution was cooled, filtered and the solvent evaporated in vacuo. The residue was subjected to column chromatography on silica gel with hexanes as the eluent to afford the title compound (0.570 g, 33% yield): 1H NMR (400 MHz, CDCl3) δ: 7.80 (1H, dd, J=7.8, 1.7 Hz), 7.49 (1H, d, J=5.4 Hz), 7.40–7.33 (3H, m), 4.78 (2H, s). LCMS (M+H)+ m/z 209.

Quelle