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

HRID 1095925Notes

Reaction equation

HRID 1095925 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[CH:22]=[CH:21][N:20]=[C:19]([CH3:23])[CH:18]=1)([OH:16])[C:12]([F:15])([F:14])[F:13].C([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]=[CH:21][N:20]=[C:19]([CH3:23])[CH:18]=1)[C:12]([F:15])([F:13])[F:14]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 252528933-(2-Chloro-4-methoxy-phenyl)-1,1,1-trifluoro-2-(2-methyl-pyridin-4-yl)-butan-2-ol

Product 1

HCID 252541463-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenolYield 88%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 3-(2-chloro-4-methoxy-phenyl)-1,1,1-trifluoro-2-(2-methyl-pyridin-4-yl)-butan-2-ol (2.77 g) in aqueous HBr (48%, 50 mL) was refluxed for 4 hours. The reaction mixture was cooled, poured into ice and basified with sat. Na2CO3 to pH 10. The aqueous phase was then extracted with ethyl acetate and the organic layer was washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate) to give the title compound as a colorless foam (2.34 g, 88%). MS (m/e)=346.1 [MH−].

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe aqueous phase was then extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate)

Sources & evidence

ORD record
ord-0c7656eec5504f198038634b8e924b8c
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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