Sodium Carbonate → 3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(5-methyl-pyrazin-2-yl)-propyl]-phenol

HRID 1095865Notes

Reaction equation

HRID 1095865 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:24])[C:11]([C:17]1[C:22](C)=[N:21][CH:20]=[CH:19][N:18]=1)([OH:16])[C:12]([F:15])([F:14])[F:13].[C:25]([O-])([O-])=O.[Na+].[Na+]>Br>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:24])[C:11]([OH:16])([C:17]1[CH:22]=[N:21][C:20]([CH3:25])=[CH:19][N:18]=1)[C:12]([F:13])([F:15])[F:14]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 66699099HCID 66699099, compound

Product 1

HCID 574212313-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(5-methyl-pyrazin-2-yl)-propyl]-phenol

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
105 °C

Procedure

3-(2-Chloro-4-methoxy-phenyl)-1,1,1-trifluoro-2-(methyl-pyrazin-2-yl)-butan-2-ol (486 mg, 1.35 mmol) was dissolved in 48% HBr (10 ml) and stirred at 105° C. (bath temperature) for 2 h. The reaction mixture was then poured on ice-water and saturated aqueous Na2CO3 and extracted twice with ethyl acetate. The combined organic phases were washed with brine, dried over Na2SO4 and evaporated in vacuo. The residue was purified by flash chromatography (10 g silica gel, ethyl acetate/heptane 9:1=>1:1) to give the title compound as white foam (375 mg). MS (m/e)=347.1 [M+H+].

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography (10 g silica gel, ethyl acetate/heptane 9:1=>1:1)

Sources & evidence

ORD record
ord-74c64ebd76a94b3bb754706830a5ace0
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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