Reacción #51202

Ecuación de reacción

2,2-Dimethyl-2,3-dihydrobenzo[b]furan

N-bromosuccinimide

ether

→

title product

Rendimiento 79.0%

5-Bromo-2,2-dimethyl-2,3-dihydrobenzo[b]furan

Rendimiento 79.0%

Disolventes

dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction was then refluxed for 2 h
2. 2
   Filtracióna white precipitate of succinimide filtered off
3. 3
   OtroThe filtrate was evaporated to dryness
4. 4
   Otropurified by column chromatography

Procedimiento

2,2-Dimethyl-2,3-dihydrobenzo[b]furan (prepared according to the method of Baker and Shulgin, J. Org. Chem., 28, 1963, 2468) (500 mg, 3.38 mmol) was taken up in dichloroethane (5.5 ml) and stirred at room temperature under nitrogen, and N-bromosuccinimide (661 mg, 3.72 mmol) added in one portion. The reaction was then refluxed for 2 h, ether was added (10 ml) and a white precipitate of succinimide filtered off. The filtrate was evaporated to dryness, and then purified by column chromatography using 5% ether in pentane as eluant to give the title product (604 mg, 79%); 1HNMR (400 MHz, CDCl3) δ: 1.43 (s, 6H), 2.92 (s, 2H), 6.54 (d, 1H), 7.16 (d, 1H), 7.19 (s, 1H); LRMS: M+H, 227. (TS+).

Fuente