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

HRID 2103782Notes

Reaction equation

HRID 2103782 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 chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
68 °C

Procedure

A 2-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 (143 g, 0.42 mole based on 97% purity) and CHCl3 (170 ml) and heated to boiling in order to dissolve. SOCl2 (38 ml, 62.1 gm, 0.52 mole) was added. The mixture was heated to reflux (68° C. final) for 4.5 hours and then stripped of volatiles to obtain 151 g yellow, turbid liquid (103% apparent yield). The material was used in the next step without further purification.

Workup

  1. customA 2-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
  6. customto obtain 151 g yellow
  7. customturbid liquid (103% apparent yield)
  8. customThe material was used in the next step without further purification

Sources & evidence

ORD record
ord-39608f30762b46359844fbde397ea000
Source dataset
uspto-grants-2009_08
Patent number
US07576131B2

Reaction notes

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