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

HRID 1095951Notes

Reaction equation

HRID 1095951 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

4

Reactant 2

HCID 25134Boron tribromideHCID 252544523-(2-Chloro-5-methoxy-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol

Product 1

HCID 252546034-Chloro-3-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenolYield 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3-(2-Chloro-5-methoxy-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol (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 dropwise 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, 81%). MS (m/e)=366.0 [MH+].

Workup

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

Sources & evidence

ORD record
ord-62cee03a53b2496984319eb90126e772
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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