Dichloromethane → 1-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride

HRID 39150

Reaction equation

HRID 39150 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([OH:15])=O)[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.C(Cl)[Cl:17].S(Cl)(Cl)=O>CN(C)C=O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([Cl:17])=[O:15])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 143496081-(1,3-Dioxaindan-5-yl)cyclopropane-1-carboxylic acid

Product 1

HCID 591291541-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an oven-dried round bottom flask containing 1-(benzo[d][1,3]dioxol-5-yl)-cyclopropanecarboxylic acid (A-8) (618 mg, 3.0 mmol) and CH2Cl2 (3 mL) was added thionyl chloride (1.07 g, 9.0 mmol) and N,N-dimethylformamide (0.1 mL). The reaction mixture was stirred at ambient temperature under an Ar atmosphere until the gas evolution ceased (2-3 h). The excess thionyl chloride was removed under vacuum and the resulting residue dissolved in CH2Cl2 (3 mL). The mixture was used without further manipulation.

Workup

  1. custom(2-3 h)
  2. customThe excess thionyl chloride was removed under vacuum
  3. dissolutionthe resulting residue dissolved in CH2Cl2 (3 mL)

Sources & evidence

ORD record
ord-149e3eca1b604a8aa9b6b65372c7188b
Source dataset
uspto-grants-2013_09
Patent number
US08524767B2

Linked notes

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