Bromine → 2-{4-[4-Bromo-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}ethanol

HRID 891118Notes

Reaction equation

HRID 891118 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][OH:15])=[CH:9][CH:8]=2)[N:5]=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:3]=1.[Br:20]Br>C(Cl)(Cl)Cl>[Br:20][C:3]1[C:4]([C:16]([F:17])([F:19])[F:18])=[N:5][N:6]([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][OH:15])=[CH:11][CH:12]=2)[C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 22244551HCID 22244551, compound

Product 1

HCID 222446842-{4-[4-Bromo-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}ethanolYield 77.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2-{4-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl} ethanol (step 450 mg, 1.67 mmol) and bromine (293 mg, 1.83 mmol) in chloroform (10 mL) was stirred at room temperature overnight. The organic solution was washed with 5% aqueous solution sodium thiosulfate, then with brine, and finally dried (Na2SO4) and evaporated. The crude product was purified by TLC with hexane/ethyl acetate (1:1) to afford 451 mg (77%) of the title compound as yellow solids: MS (EI) m/z 348 [M]+, 1H-NMR (CDCl3) δ 7.37 (4H, s), 3.89 (2H, br.s), 2.94 (2H, t, J=6.4 Hz), 2.33 (3H, s).

Workup

  1. washThe organic solution was washed with 5% aqueous solution sodium thiosulfate
  2. dry with materialwith brine, and finally dried (Na2SO4)
  3. customevaporated
  4. customThe crude product was purified by TLC with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-b039a660e8a940228125be927aedc0c2
Source dataset
uspto-grants-2006_02
Patent number
US07001917B2

Reaction notes

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