Thionyl Chloride → 2-{4-[4-(Trifluoromethyl)phenoxy]phenoxy}propanoyl chloride
Reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]([F:27])([F:26])[C:7]1[CH:25]=[CH:24][C:10]([O:11][C:12]2[CH:23]=[CH:22][C:15]([O:16][CH:17]([CH3:21])[C:18](O)=[O:19])=[CH:14][CH:13]=2)=[CH:9][CH:8]=1>>[F:5][C:6]([F:27])([F:26])[C:7]1[CH:25]=[CH:24][C:10]([O:11][C:12]2[CH:23]=[CH:22][C:15]([O:16][CH:17]([CH3:21])[C:18]([Cl:3])=[O:19])=[CH:14][CH:13]=2)=[CH:9][CH:8]=1Participants
Procedure
Thionyl chloride (4.4 parts by volume) was added to 3.26 parts of 2-[4-(4-trifluoromethylphenoxy)phenoxy]propionic acid, and the mixture was refluxed for 3 hours. After the reaction, the excess of thionyl chloride was removed under reduced pressure to give 2-[4-(4-trifluoromethylphenoxy)phenoxy]propionyl chloride. A solution of the resulting propionyl chloride in 10 parts by volume of ether was added dropwise under ice cooling to a solution of 3.34 parts of diethyl aminophosphonate in 20 parts by volume of ether. Ten minutes later, 1 part by volume of triethylamine was added dropwise. After the addition, the mixture was stirred at room temperature for 3 hours. The reaction mixture was washed with water, a saturated aqueous solution of sodium bicarbonate and water in this order. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 2.6 parts of a crude product. The crude product was recrystallized from ethyl acetate/ether to give 1.1 parts of the captioned compound. This compound had a melting point of 134.5° to 135° C., and its IR and NMR spectral data are shown in Table 1.
Workup
- temperaturethe mixture was refluxed for 3 hours
- customAfter the reaction
- customthe excess of thionyl chloride was removed under reduced pressure
Sources & evidence
- ORD record
- ord-e34b2798a05b4eca874a848715341f1f
- Source dataset
- uspto-grants-1989_06
- Patent number
- US04838923
Reaction notes
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