反応 #1552104

反応方程式

5-bromo-N-(4-bromophenyl)-2-nitrosoaniline

Water

→

2,7-dibromophenazine

収率 16.0%

溶媒

AcOH

反応条件

後処理

1. 1
   温度under reflux for 1.5 hrs
2. 2
   その他the brown precipitate formed
3. 3
   ろ過was collected by filtration
4. 4
   洗浄after washing with water (2×200 mL)
5. 5
   その他The product was purified by silica gel chromatography (SiO2, hexanes/DCM=1/1(v/v))

実験手順

5-bromo-N-(4-bromophenyl)-2-nitrosoaniline (13-1) (10 g, 28.1 mmol) in AcOH (300 mL) was heated under reflux for 1.5 hrs. Water (400 mL) was then added and the brown precipitate formed was collected by filtration after washing with water (2×200 mL). The product was purified by silica gel chromatography (SiO2, hexanes/DCM=1/1(v/v)) to afford a brown solid, 2,7-dibromophenazine 13-2 (1.52 g, 16% yield). 1H NMR (CDCl3): δ 8.43 (2H, dd, J 2.2, 0.4 Hz), 8.10 (2H, dd, J 9.2, 0.4 Hz), 7.91 (2H, dd, J 9.2, 2.2 Hz) ppm. LC-MS (ESI): m/z 338.6 [M+H]+.

出典