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

HRID 333809Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[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].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[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: 0 °C

Procedure

3-(2-Chloro-5-methoxy-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol (Example 115, 293 mg) was dissolved in CH2Cl2 (30 mL) and cooled to 0° C. A solution of boron tribromide (1M in CH2Cl2, 3.08 mL) was added drop wise and stirring was continued at 0° C. for 1 hour. The reaction mixture was diluted with CH2Cl2, extracted with sat. NaHCO3 solution and brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (silica gel, ethyl acetate in heptane 3:7) to give the title compound as a colorless solid (230 mg). MS (m/e)=366.0 (MH+).

Workup

extractionextracted with sat. NaHCO3 solution and brine
dry with materialdried over Na2SO4
customevaporated
customThe residue was purified by flash chromatography (silica gel, ethyl acetate in heptane 3:7)

Sources & evidence

ORD record: ord-9ed551d08e6048578f7cd71d4684ba9e
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883786B2

Reaction notes

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