Thionyl Chloride → 1-(3,4-Dichloro-phenyl)-cyclopropanecarbonyl chloride

HRID 32501Notes

Reaction equation

HRID 32501 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:12]([OH:14])=O)[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].S(Cl)([Cl:17])=O>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:12]([Cl:17])=[O:14])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 5755341-(3,4-Dichlorophenyl)cyclopropanecarboxylic acid

Product 1

HCID 865957291-(3,4-Dichloro-phenyl)-cyclopropanecarbonyl chloride

Procedure

1-(3,4-Dichloro-phenyl)-cyclopropanecarboxylic acid (1 g, 4.35 mmol) was stirred in thionyl chloride (2 ml) at 37° for 72 h then the thionyl chloride was removed under reduced pressure the residue was rotovapped from benzene (×3) affording the title compound as a yellow oil. (1.1 g, quant) 1H NMR(400 MHz, CDCl3) δ 7.46 (dd, J=8.3 Hz, 4.4 Hz, 2H), 7.23 (d, J=8.3, 1H), 2.00 (dd, J=4.6, Hz, 7.6 Hz, 2H), 1.485(dd, J=4.6, Hz, 7.6 Hz, 2H).

Workup

  1. customthe thionyl chloride was removed under reduced pressure the residue

Sources & evidence

ORD record
ord-cef6b55364ae4b6f8bfc0fed12542a55
Source dataset
uspto-grants-2008_09
Patent number
US07427623B2

Reaction notes

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