Thionyl Chloride → [3-Chloro-5-(3-chloro-5-cyanophenoxy)phenoxy]acetyl chloride

HRID 1157395Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([O:13][C:14]2[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[C:16]([Cl:22])[CH:15]=2)[CH:12]=1)[O:5][CH2:6][C:7](O)=[O:8].S(Cl)([Cl:25])=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([O:13][C:14]2[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[C:16]([Cl:22])[CH:15]=2)[CH:12]=1)[O:5][CH2:6][C:7]([Cl:25])=[O:8]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 59511727[3-Chloro-5-(3-chloro-5-cyanophenoxy)phenoxy]acetic acid

Product 1

HCID 59511713[3-Chloro-5-(3-chloro-5-cyanophenoxy)phenoxy]acetyl chloride

Procedure

190 mg (0.562 mmol) of [3-chloro-5-(3-chloro-5-cyanophenoxy)phenoxy]acetic acid (5-3) was refluxed in an excess of thionyl chloride for 5 hours. After this time the reaction was cooled and the thionyl chloride was removed in vacuo and the resultant oil solidified upon storage under reduced pressure to yield the desired product 5-4. 1H NMR(CDCl3): 4.94 (s, 2H), 6.49 (m, 1H), 6.71 (m, 1H), 6.74 (m, 1H), 7.16 (m, 1H), 7.23 (m, 1H), 7.41 (m, 1H).

Workup

temperatureAfter this time the reaction was cooled
customthe thionyl chloride was removed in vacuo

Sources & evidence

ORD record: ord-1c6b604c4af242a9b6cfd0ac430f10e3
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807684B2

Reaction notes

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