反応 #1552099

反応方程式

bromoacetyl chloride

9H-xanthene

AlCl3

→

1,1′-(9H-xanthene-2,7-diyl)bis(2-bromoethanone)

収率 36.7%

溶媒

DCM

反応条件

後処理

1. 1
   workup.WAITleft
2. 2
   workup.ADDITIONThe reaction mixture was poured onto ice (400 mL)
3. 3
   抽出extracted with DCM (2×200 mL)
4. 4
   洗浄The combined organic phase was washed with brine (400 mL)
5. 5
   乾燥dried over MgSO4
6. 6
   ろ過filtered
7. 7
   その他evaporated to dryness
8. 8
   その他The crude material was precipitated in EtOAc
9. 9
   ろ過filtered

実験手順

Referring to Scheme 5, bromoacetyl chloride (4.59 ml, 54.9 mmol) was added dropwise to a solution of 9H-xanthene (5 g, 27.4 mmol) and AlCl3 (8.05 g, 60.4 mmol), DCM (100 mL) at 0° C. The reaction mixture was allowed to warm up to rt and left to stir for 72 hrs. The reaction mixture was poured onto ice (400 mL), extracted with DCM (2×200 mL). The combined organic phase was washed with brine (400 mL), dried over MgSO4, filtered and evaporated to dryness. The crude material was precipitated in EtOAc and filtered to give 1,1′-(9H-xanthene-2,7-diyl)bis(2-bromoethanone) (5-2) as a white solid (4.27 g, 36.7% yield). LC-MS (ESI): m/z 425.9 [M+H]+.

出典