Dimethylformamide → 2,2-Difluoro-1,3-benzodioxole-4-carbonyl chloride

HRID 2395552Notes

Reaction equation

HRID 2395552 reaction equation
[F:1][C:2]1([F:14])[O:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11](O)=[O:12])[C:4]=2[O:3]1.CN(C)C=O.S(Cl)([Cl:22])=O>ClCCCl>[F:1][C:2]1([F:14])[O:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([Cl:22])=[O:12])[C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 27740672,2-Difluoro-1,3-dioxaindane-4-carboxylic acid

Product 1

HCID 27740622,2-Difluoro-1,3-benzodioxole-4-carbonyl chlorideYield 106%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2,2-Difluoro-1,3-benzodioxole-4-carboxylic acid (15.0 g) was dissolved in 1,2-dichloroethane and N,N-dimethylformamide and thionyl chloride (10.6 g) added. The mixture was heated under reflux for 1 hour, and the solvent evaporated in vacuo. The residue was dissolved in toluene and re-evaporated to yield 2,2-difluoro-1,3-benzodioxol-4-oyl chloride (17.35 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customthe solvent evaporated in vacuo
  4. dissolutionThe residue was dissolved in toluene
  5. customre-evaporated

Sources & evidence

ORD record
ord-6f602d286afe4f3d9c9cd1f5dfbb0e88
Source dataset
uspto-grants-1996_02
Patent number
US05489570

Reaction notes

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