Sodium Carbonate → 4-bromo-5-(tert-butyl-dimethyl-silanyloxymethyl)-1-methyl-3-(4-trifluoromethyl-phenyl)-1H-pyrazole

HRID 915413Notes

Reaction equation

HRID 915413 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:25])([CH3:24])[C:8]1[N:12]([CH3:13])[N:11]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[Br:26]Br.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Br:26][C:9]1[C:10]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:22])([F:21])[F:23])=[CH:18][CH:19]=2)=[N:11][N:12]([CH3:13])[C:8]=1[C:7]([CH3:25])([CH3:24])[O:6][SiH2:5][C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24408BromineHCID 1317265825-(Tert-butyl-dimethyl-silanyloxymethyl)-1-methyl-3-(4-trifluoromethyl-phenyl)-1h-pyrazole

Product 1

HCID 1317265814-bromo-5-(tert-butyl-dimethyl-silanyloxymethyl)-1-methyl-3-(4-trifluoromethyl-phenyl)-1H-pyrazoleYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

A solution of 5-(tert-butyl-dimethyl-silanyloxymethyl)-1-methyl-3-(4-trifluoromethyl-phenyl)-1H-pyrazole (162 mg, 437 μmol) in dichloromethane (1.7 ml) was added within 10 min to a mixture of bromine (20 μl, 480 μmol) and sodium carbonate (93 mg, 880 μmol) in dichloromethane (4.3 ml) at 0° C. under an argon atmosphere. After stirring at 0 to 5° C. for 1 h and then at ambient temperature for 1 h, the mixture was quenched with water (5 ml) and extracted two times with dichloromethane. The combined extracts were washed with aqueous saturated NaHSO3 solution and brine/ice water 1/1 and dried over sodium sulfate. Removal of the solvent under reduced pressure left off-white crystals which were purified by column chromatography (silica gel, heptane/AcOEt) to give 90 mg (0.2 mmol, 46%) of the title compound as colorless crystals.

Workup

  1. waitat ambient temperature for 1 h
  2. customthe mixture was quenched with water (5 ml)
  3. extractionextracted two times with dichloromethane
  4. washThe combined extracts were washed with aqueous saturated NaHSO3 solution and brine/ice water 1/1
  5. dry with materialdried over sodium sulfate
  6. customRemoval of the solvent under reduced pressure
  7. waitleft off-white crystals which
  8. customwere purified by column chromatography (silica gel, heptane/AcOEt)

Sources & evidence

ORD record
ord-f704ff9257674dde9db73ac3ccbd0b98
Source dataset
uspto-grants-2007_09
Patent number
US07265149B2

Reaction notes

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