Thionyl Chloride → 2-[5-(4-Chlorophenyl)-2-ethylphenyl]-2-oxoacetyl chloride

HRID 335455Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:19][CH3:20])=[C:12]([C:14](=[O:18])[C:15](O)=[O:16])[CH:13]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:23])=O>CN(C)C=O.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:19][CH3:20])=[C:12]([C:14](=[O:18])[C:15]([Cl:23])=[O:16])[CH:13]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a 20 ml volume three-necked flask, 2-[5-(4-chlorophenyl)-2-ethylphenyl]-2-oxoacetic acid (8-c) (1.01 g), toluene (3.5 ml), dimethylformamide (3 drops), and thionyl chloride (624 mg) were added under a nitrogen atmosphere, and stirred at 50° C. for 3 hours. The mixture was concentrated under reduced pressure, and azeotropic-distilled with toluene 3 times to give 937 mg of 2-[5-(4-chlorophenyl)-2-ethylphenyl]-2-oxoacetyl chloride (6-c).

Workup

concentrationThe mixture was concentrated under reduced pressure
distillationazeotropic-distilled with toluene 3 times

Sources & evidence

ORD record: ord-9db1dcce6a5c48eebd928d188d0bcfde
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08884010B2

Reaction notes

Loading…