Hydrochloric Acid → 4-((3-Fluoro-5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy propanoic acid

HRID 232248Notes

Reaction equation

[OH:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH:7]([CH3:11])[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].Br[C:17]1[C:22]([F:23])=[CH:21][C:20]([C:24]([F:27])([F:26])[F:25])=[CH:19][N:18]=1.Cl>CS(C)=O.O>[F:23][C:22]1[C:17]([O:1][C:2]2[CH:3]=[CH:4][C:5]([O:6][CH:7]([CH3:11])[C:8]([OH:10])=[O:9])=[CH:12][CH:13]=2)=[N:18][CH:19]=[C:20]([C:24]([F:26])([F:25])[F:27])[CH:21]=1

Participants

Conditions

Temperature: 48 °C

Procedure

2-(4-Hydroxyphenoxy) propanoic acid (1.80 g, 0.00988 mole) was dissolved in 15 ml of dimethyl sulfoxide. A solution of sodium hydroxide (0.8 g, 0.02 mole in 1 ml of water) was added and the reaction mixture was heated under nitrogen to 48° C. over a 27 minute period. 2-Bromo-3-fluoro-5-(trifluoromethyl)pyridine (2.40 g, 0.00984 mole) dissolved in 5 ml of dimethyl sulfoxide was added and the reaction mixture was heated at 75°-78° C. for 40 minutes. The mixture was poured into 150 ml of cold water and acidified with aqueous HCl. A gum came down. Upon work-up and purification, a fraction (0.45 g) was obtained which had an elemental analysis of, in percent by weight:

Workup

additionwas added
temperaturethe reaction mixture was heated at 75°-78° C. for 40 minutes
customUpon work-up and purification
customa fraction (0.45 g) was obtained which

Sources & evidence

ORD record: ord-8044d02296de4681a066f97b9268b0ef
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04851539

Reaction notes

Loading…