Potassium Carbonate → ((2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluorophenyl)methoxy)acetic acid, 1-methylethyl ester

HRID 1440151Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2[C:13]([Cl:14])=[C:12]([C:15]([F:18])([F:17])[F:16])[N:11]([CH3:19])[N:10]=2)=[CH:4][C:3]=1[CH2:20][OH:21].C([O-])([O-])=O.[K+].[K+].Br[CH2:29][C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31]>CS(C)=O.O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2[C:13]([Cl:14])=[C:12]([C:15]([F:16])([F:17])[F:18])[N:11]([CH3:19])[N:10]=2)=[CH:4][C:3]=1[CH2:20][O:21][CH2:29][C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31]

Participants

Conditions

Temperature: 45 °C

Procedure

At 25° C., 1.7 g (5.0 mmole) 2-chloro-5-[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzenemethanol, 0.8 g (5.5 mmole) K2CO3 and 0.7 mL (5.5 mmole) isopropyl bromoacetate were slurried in 15 mL DMSO. The mixture was stirred overnight at 45° C. The mixture was cooled, diluted with 100 mL cold water and extracted four times with ethyl acetate. The ethyl acetate extracts were washed with brine, dried over anhydrous MgSO4 and stripped in vacuo. The residue was purified chromatographically using 10% ethyl acetate in hexane as the eluent to give 0.9 g (41%) of ((2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluorophenyl)methoxy)acetic acid, 1-methylethyl ester as a white solid; mp 55° C.

Workup

customAt 25° C.
temperatureThe mixture was cooled
extractionextracted four times with ethyl acetate
washThe ethyl acetate extracts were washed with brine
dry with materialdried over anhydrous MgSO4
customThe residue was purified chromatographically

Sources & evidence

ORD record: ord-b15fd6e13f804010b253e2ab0c9702f1
Source dataset: uspto-grants-1996_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05496956

Reaction notes

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