Water → 3-Chloro-4-[(5-trifluoromethylpyridin-2-yl)oxy]phenylacetic acid

HRID 963303Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].Cl[C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=1.O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[O:8][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=1

Participants

Conditions

Temperature: 100 °C

Procedure

9.3 g (50 mmol) of 3-chloro-4-hydroxylphenylacetic acid was dissolved in 100 ml of N,N-dimethylformamide, and 15.2 g (110 mmol) of potassium carbonate was added thereto. The mixture was stirred at 100° C. for one hour. Then, 10.9 g (60 mmol) of 2-chloro-5-trifluoromethylpyridine was added thereto, and the mixture was stirred for 8 hours at 120° C. After cooling, the reaction solution was poured into water and washed twice with ethyl acetate. The obtained aqueous layer was adjusted to pH 4 with citric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. Then, ethyl acetate was distilled off under reduced pressure. The obtained residue was recrystallized from ethanol to obtain 8.3 g of the desired product as a white powder (melting point: 138° to 139° C.).

Workup

stirringthe mixture was stirred for 8 hours at 120° C
temperatureAfter cooling
washwashed twice with ethyl acetate
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
distillationThen, ethyl acetate was distilled off under reduced pressure
customThe obtained residue was recrystallized from ethanol

Sources & evidence

ORD record: ord-5a7c6b5f34984503855b50b2ac744084
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05763463

Reaction notes

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