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

HRID 1095876Notes

Reaction equation

HRID 1095876 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]([Cl:23])[CH:18]=1)([OH:16])[C:12]([F:15])([F:14])[F:13].C([O-])(O)=O.[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]([C:17]1[CH:22]=[CH:21][N:20]=[C:19]([Cl:23])[CH:18]=1)([OH:16])[C:12]([F:15])([F:14])[F:13]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 574212633-(2-Chloro-4-methoxy-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol

Product 1

HCID 574212643-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenolYield 97.3%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
105 °C

Procedure

3-(2-Chloro-4-methoxy-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol (13.35 g, 0.0351 mol) was dissolved in 48% HBr (250 ml) and stirred at 105° C. (bath temperature) for 7 h. The mixture was poured on ice-water-brine and saturated aqueous NaHCO3 and extracted with AcOEt. The combined organic phases were washed with brine, dried over MgSO4, and evaporated in vacuo. The residue foam was treated with heptane over night. The precipitation was filtered and dried to give the title compound (12.5 g) as a white solid. MS (m/e, ISP neg. ion)=364.3 [M−H+].

Workup

  1. extractionextracted with AcOEt
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. additionThe residue foam was treated with heptane over night
  6. customThe precipitation
  7. filtrationwas filtered
  8. customdried

Sources & evidence

ORD record
ord-e1db5d02b3c541b69c3beadc12f517f9
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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