Ethyl bromoacetate → (4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-5-fluoro-2-nitrophenoxy)acetic acid, ethyl ester

HRID 2395650Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:12]2[C:17]([F:18])=[CH:16][C:15]([OH:19])=[C:14]([N+:20]([O-:22])=[O:21])[CH:13]=2)=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8].C([O-])([O-])=O.[K+].[K+].Br[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32]>CC(C)=O.O>[Cl:1][C:2]1[C:3]([C:12]2[C:17]([F:18])=[CH:16][C:15]([O:19][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:14]([N+:20]([O-:22])=[O:21])[CH:13]=2)=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:8])[F:9]

Participants

Conditions

Temperature: 40 °C

Procedure

At 25° C., 6.11 g (0.018 mole) 4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-5-fluoro-2-nitrophenol, 2.5 g (0,019 mole) K2CO3, and 2.0 mL (0.019 mole) ethyl bromoacetate were slurried in 100 mL acetone. The reaction mixture was stirred at 40° C. for 4 hours. 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 recrystallized from methylcyclohexane to give 7.5 g (99%) of (4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-5-fluoro-2-nitrophenoxy)acetic acid, ethyl ester as a light yellow solid, mp 95°-96° 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 recrystallized from methylcyclohexane

Sources & evidence

ORD record: ord-9bed0eb827574a3f95f83d253adae93a
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05489571

Reaction notes

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