Thionyl Chloride → 2-[2-Nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionyl Chloride

HRID 1995035

Reaction equation

[N+:1]([C:4]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=2[Cl:27])=[CH:12][C:5]=1[O:6][CH:7]([CH3:11])[C:8](O)=[O:9])([O-:3])=[O:2].S(Cl)([Cl:30])=O>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=2[Cl:27])=[CH:12][C:5]=1[O:6][CH:7]([CH3:11])[C:8]([Cl:30])=[O:9])([O-:3])=[O:2]

Participants

Conditions

Temperature: 67 °C

Procedure

2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionic acid (100 grams) and toluene (40 ml) were charged into a glass reaction vessel equipped with a magnetic stirrer. The mixture was heated on a steam bath until a solution was obtained. The solution was allowed to cool and thionyl chloride (100 ml) was added dropwise with stirring. After the addition was completed, the mixture was warmed to 67° C. with continued stirring for a period of about 21/2 hours. After this time the mixture was stripped of solvent in a rotary evaporator under reduced pressure leaving as the residue 105 grams of the desired product, 2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionyl chloride as a burgundy colored viscous oil.

Workup

customequipped with a magnetic stirrer
temperatureThe mixture was heated on a steam bath until a solution
customwas obtained
temperatureto cool
additionAfter the addition
stirringwith continued stirring for a period of about 21/2 hours
customAfter this time the mixture was stripped of solvent in a rotary evaporator under reduced pressure

Sources & evidence

ORD record: ord-f6e812eecfe14b80af0abbeb1904c913
Source dataset: uspto-grants-1983_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04402729

Linked notes

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