Réaction #1552103

Équation de réaction

2,7-dibromodibenzo[b,f]oxepine

→

2,7-dibromo-10,11-dihydrodibenzo[b,f]oxepine

Rendement 81.4%

Solvants

EtOAc

—

petroleum ether

Conditions de réaction

Traitement

1. 1
   Autrethe reaction was evacuated
2. 2
   AutreAfter 2 h reaction mixture
3. 3
   Autrewas degassed
4. 4
   Filtrationfiltered through Celite®545 (eluant EtOAc) and solvent
5. 5
   Autrewas removed in vacuo
6. 6
   Autreto give a yellow oil
7. 7
   Lavageeluting with isohexanes 400 mL
8. 8
   AutreSolvent was removed in vacuo

Mode opératoire

A solution of 2,7-dibromodibenzo[b,f]oxepine (10-2) (663 mg, 1.88 mmol) in EtOAc (40 mL) was degassed under N2. Pt/C 10% by wt (200 mg) was added and the reaction was evacuated and placed under H2 gas. After 2 h reaction mixture was degassed and filtered through Celite®545 (eluant EtOAc) and solvent was removed in vacuo to give a yellow oil. The compound was dissolved in petroleum ether and passed through a short pad of SiO2, eluting with isohexanes 400 mL. Solvent was removed in vacuo, to give 2,7-dibromo-10,11-dihydrodibenzo[b,f]oxepine (10-3) (542 mg, 81% yield) as a colorless oil. 1H NMR (CDCl3): δ 7.33-7.32 (1H, m), 7.29-7.24 (2H, m), 7.18-7.14 (1H, m), 7.04-6.96 (2H, m), 3.08 (4H, s) ppm.

Source