tert-Butyl bromoacetate → HCID 68509507, compound

HRID 1927814Notes

Reaction equation

HRID 1927814 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[F:10][C:11]([F:23])([F:22])[C:12]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][NH:14][N:13]=1.C(=O)(O)[O-].[Na+]>ClCCl>[C:6]([O:5][C:3](=[O:4])[CH2:2][N:14]1[CH:15]=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([C:11]([F:10])([F:22])[F:23])=[N:13]1)([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 516892Sodium BicarbonateHCID 178469923HCID 178469923, compound

Product 1

HCID 68509507HCID 68509507, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

404 mg of Hünig-base and 469 mg of tert-butyl bromoacetate, dissolved in 2 ml of dichloromethane, are added to a solution of 50 mg of ethyl 3-(trifluoromethyl)-1H-pyrazole-4-carboxylate in 10 ml of dichloromethane. The mixture is stirred at room temperature for 16 hours. After addition of saturated sodium bicarbonate solution, the mixture is extracted with ethyl acetate, the organic phase is separated off and dried over sodium sulphate and the solvent is removed under reduced pressure. This gives 742 mg of ethyl 1-(2-tert-butoxy-2-oxoethyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate (Va-10) in a purity of about 78% (LCMS).

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. customthe organic phase is separated off
  3. dry with materialdried over sodium sulphate
  4. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-d30f2fe089ec4c369102fc79989bece5
Source dataset
uspto-grants-2012_05
Patent number
US08183351B2

Reaction notes

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