Reaktion #51202

Reaktionsgleichung

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

N-bromosuccinimide

ether

→

title product

Ausbeute 79.0%

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

Ausbeute 79.0%

Lösungsmittel

dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was then refluxed for 2 h
2. 2
   Filtrationa white precipitate of succinimide filtered off
3. 3
   SonstigeThe filtrate was evaporated to dryness
4. 4
   Sonstigepurified by column chromatography

Vorschrift

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+).

Quelle