Reaktion #171648

Reaktionsgleichung

N-Bromosuccinimide

4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepine

water

→

2-bromo-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepine

Ausbeute 65.4%

Lösungsmittel

dimethylformamide

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with 20 ml of ethylacetate twice
2. 2
   WaschenCombined organic extracts were washed with water and brine
3. 3
   Trocknendried over MgSO4
4. 4
   SonstigeThe solvent was evaporated

Vorschrift

N-Bromosuccinimide (0.237 g, 1.33 mmol) in dimethylformamide (4 mL) was added dropwise to a solution of 4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepine (0.250 g, 1.23 mmol) in dimethylformamide (4 mL, 100 mmol) at 0° C. The reaction mixture was stirred for 18 hours at room temperature. The reaction mixture was mixed with 40 ml of water and extracted with 20 ml of ethylacetate twice. Combined organic extracts were washed with water and brine, and dried over MgSO4. The solvent was evaporated affording 2-bromo-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepine (0.227 g, 63%). 1H NMR (500 MHz, CDCl3) 8.76 (s, 1H), 8.26 (d, J=5.4, 1H), 6.90 (d, J=5.5, 1H), 6.88 (s, 1H), 4.36 (t, J=4.7, 2H), 3.19 (t, J=4.8, 2H). MS (ESI+) 282.0

Quelle