Réaction #1552099

Équation de réaction

bromoacetyl chloride

9H-xanthene

AlCl3

→

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

Rendement 36.7%

Solvants

DCM

Conditions de réaction

Traitement

1. 1
   workup.WAITleft
2. 2
   workup.ADDITIONThe reaction mixture was poured onto ice (400 mL)
3. 3
   Extractionextracted with DCM (2×200 mL)
4. 4
   LavageThe combined organic phase was washed with brine (400 mL)
5. 5
   Séchagedried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Autreevaporated to dryness
8. 8
   AutreThe crude material was precipitated in EtOAc
9. 9
   Filtrationfiltered

Mode opératoire

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]+.

Source