Sodium hydride → (4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-5-fluoro-2-nitrophenoxy)acetic acid, butyl ester

HRID 1440133Notes

Reaction equation

HRID 1440133 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[C:15](F)=[CH:14][C:13]=2[F:22])=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8].[C:23]([O:27][CH2:28][CH2:29][CH2:30][CH3:31])(=[O:26])[CH2:24][OH:25].[H-].[Na+]>C1COCC1>[Cl:1][C:2]1[C:3]([C:12]2[C:13]([F:22])=[CH:14][C:15]([O:25][CH2:24][C:23]([O:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:26])=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=2)=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81882Butyl GlycolateHCID 152785734-chloro-3-(2,4-difluoro-5-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole

Product 1

HCID 15278575(4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-5-fluoro-2-nitrophenoxy)acetic acid, butyl esterYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3.4 g (0.01 mole) 4-chloro-3-(2,4-difluoro-5-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole and 1.4 mL (0.011 mole) butyl glycolate in 25 mL anhydrous THF was chilled to 0° C. Maintaining the temperature below 5° C., 0.33 g (0.011 mole) NaH was added in portions. Once the addition was completed, the reaction mixture was allowed to warm to 25° C. After 3 hours the mixture was carefully quenched with water and extracted with ethyl acetate. The ethyl acetate extracts were washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified chromatographically with 20% ethyl acetate/hexanes to yield 3.25 g (72%) (4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-5-fluoro-2-nitrophenoxy)acetic acid, butyl ester as a light yellow solid; mp 65° C.

Workup

  1. additionwas added in portions
  2. additionOnce the addition
  3. customAfter 3 hours the mixture was carefully quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate extracts were washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified chromatographically with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-72ec07bb971e4f5e9a3c8f824b667d04
Source dataset
uspto-grants-1996_03
Patent number
US05496956

Reaction notes

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