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

HRID 333822Notes

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

Conditions

Temperature: 105 °C

Procedure

3-(2-Chloro-4-methoxy-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol (Example 132, 48 mg) was dissolved in 48% aqueous HBr (0.9 m) and stirred at 105° C. (bath temperature) for 4 h. The reaction mixture was then poured on ice-water-brine and sat aq NaHCO3 and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over MgSO4 and evaporated in vacuo. The resulting brown residue was purified by flash chromatography (8 g silica gel, ethyl acetate/heptane 1:4) to give the title compound as off-white semisolid (34 mg). MS (m/e)=364.0 (M−H).

Workup

additionThe reaction mixture was then poured on ice-water-brine
extractionextracted with ethyl acetate
washThe combined organic phases were washed with brine
dry with materialdried over MgSO4
customevaporated in vacuo
customThe resulting brown residue was purified by flash chromatography (8 g silica gel, ethyl acetate/heptane 1:4)

Sources & evidence

ORD record: ord-d161696edbe645ee986e4118f6df41a0
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883786B2

Reaction notes

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