Thionyl Chloride → 4-Chloro-α-[3-(trifluoromethyl)phenoxy]benzeneacetyl chloride

HRID 1805302Notes

Reaction equation

HRID 1805302 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[C:9](O)=[O:10])=[CH:4][CH:3]=1.O=S(Cl)[Cl:25]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[C:9]([Cl:25])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 99494114687-08-5

Product 1

HCID 121092354-Chloro-α-[3-(trifluoromethyl)phenoxy]benzeneacetyl chlorideYield 107.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

A 3-L evaporation flask with magnetic stirrer, Claissen adapter, pot thermometer and a reflux condenser routed to a gas scrubber was charged with (+) 4-chlorophenyl-(3-trifluoromethylphenoxy)-acetic acid (131 g, 0.37 mole) and CHCl3 (152 ml) and heated to boiling in order to dissolve. SOCl2 (35 ml, 56.5 g, 0.48 mole) was added. The mixture was heated to reflux (70° C. final) for 4 hours and then stripped of volatiles to obtain 139 g liquid. The material was used in the next step without further purification.

Workup

  1. customA 3-L evaporation flask with magnetic stirrer
  2. customClaissen adapter, pot thermometer and a reflux condenser routed to a gas scrubber
  3. temperatureheated
  4. dissolutionto dissolve
  5. temperatureThe mixture was heated

Sources & evidence

ORD record
ord-e54277eac4c4478c9153cba8a6ab0b62
Source dataset
uspto-grants-2013_01
Patent number
US08354448B2

Reaction notes

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