Chlorosuccinimide → Methyl 7-chloro-2,3-dihydro-8-methoxy-1,4-benzodioxin-5-carboxylate
Reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][CH2:10][CH2:11][O:12][C:7]=2[C:6]([C:13]([O:15][CH3:16])=[O:14])=[CH:5][CH:4]=1.[Cl:17]N1C(=O)CCC1=O>C(#N)C>[Cl:17][C:4]1[CH:5]=[C:6]([C:13]([O:15][CH3:16])=[O:14])[C:7]2[O:12][CH2:11][CH2:10][O:9][C:8]=2[C:3]=1[O:2][CH3:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of intermediate (1) (0.118 mol) and N-chlorosuccinimide (0.125 mol) in ACN (350 ml) was stirred at room temperature for two days. The solvent was evaporated and the residue was partitioned between DCM (500 ml) and water (500 ml). The organic layer was separated, dried, filtered and the solvent was evaporated. A part of the residue was crystallized from a mixture of DIPE and ACN, yielding methyl 7-chloro-2,3-dihydro-8-methoxy-1,4-benzodioxin-5-carboxylate (intermediate 2, mp. 99° C.)