Chlorosuccinimide → Methyl 7-chloro-2,3-dihydro-8-methoxy-1,4-benzodioxin-5-carboxylate

HRID 1868355Notes

Reaction equation

HRID 1868355 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

HCID 31398ChlorosuccinimideHCID 11637164HCID 11637164, compound

Product 1

HCID 11565132Methyl 7-chloro-2,3-dihydro-8-methoxy-1,4-benzodioxin-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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.)

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between DCM (500 ml) and water (500 ml)
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customA part of the residue was crystallized from a mixture of DIPE and ACN

Sources & evidence

ORD record
ord-ac8a1a8dcfe64a0db7b999b733f439bf
Source dataset
uspto-grants-2009_12
Patent number
US07635706B2

Reaction notes

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