Sodium Hydroxide → 4-((3-Fluoro-5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy propanoic acid

HRID 232249Notes

Reaction equation

F[C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[OH:13][C:14]1[CH:25]=[CH:24][C:17]([O:18][CH:19]([CH3:23])[C:20]([OH:22])=[O:21])=[CH:16][CH:15]=1.[OH-].[Na+]>O=S(Cl)Cl>[F:8][C:7]1[C:2]([O:13][C:14]2[CH:15]=[CH:16][C:17]([O:18][CH:19]([CH3:23])[C:20]([OH:22])=[O:21])=[CH:24][CH:25]=2)=[N:3][CH:4]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:6]=1

Participants

Conditions

Temperature: 115 °C

Procedure

A fresh sample of 2-(4-((3-fluoro-5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy propanoic acid was prepared by the reaction of 2,3-difluoro-5-(trifluoromethyl)pyridine with 2-(4-hydroxyphenoxy)propanoic acid in the presence of 2 moles of sodium hydroxide as above described and 9.0 g (0.026 mole) was refluxed in excess SOCl2 for about 1/2 hour to prepare the corresponding acid chloride. The excess SOCl2 was removed by heating to 115° C. under an aspirator vacuum. The resulting acid chloride was added to a mixture of concentrated ammonium hydroxide (30 ml) and methanol (60 ml). The flask was rinsed with an additional 15 ml ammonium hydroxide mixed with about 25 ml of methanol and the two fractions were combined. The acid amide formed as a solid which was filtered out, rinsed with water, slurried in water, filtered, dried and analyzed. M.P. 140°-141° C.

Workup

customThe excess SOCl2 was removed
additionThe resulting acid chloride was added to a mixture of concentrated ammonium hydroxide (30 ml) and methanol (60 ml)
washThe flask was rinsed with an additional 15 ml ammonium hydroxide
additionmixed with about 25 ml of methanol

Sources & evidence

ORD record: ord-12d62d18bc2d4cfeb3209f6bfb785ee3
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04851539

Reaction notes

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