Triethylsilane → HCID 59235389, compound

HRID 2174345Notes

Reaction equation

HRID 2174345 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:20])=[C:6]([C:8]([C:10]2[CH:15]=[C:14]([F:16])[C:13]([O:17][CH3:18])=[C:12]([F:19])[CH:11]=2)=O)[CH:7]=1.C([SiH](CC)CC)C.FC(F)(F)S(O)(=O)=O>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:20])=[C:6]([CH:7]=1)[CH2:8][C:10]1[CH:15]=[C:14]([F:16])[C:13]([O:17][CH3:18])=[C:12]([F:19])[CH:11]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 62406Trifluoromethanesulfonic acidHCID 59235372HCID 59235372, compound

Product 1

HCID 59235389HCID 59235389, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (5-bromo-2-chlorophenyl)(3,5-difluoro-4-methoxy-phenyl)methanone (629 mg, 1.7 mmol) in trifluoroacetic acid (6 mL) was added triethylsilane (1.1 mL, 6.9 mmol), and the mixture was stirred for 10 minutes at 25° C. Trifluoromethane-sulfonic acid (50 μL) was added, and the reaction was briefly boiled. The mixture was stirred overnight at 25° C. before the volatiles were removed under reduced pressure. The residue was dissolved in ethyl acetate (20 mL) and was washed with saturated sodium carbonate and brine, dried over sodium sulfate, and concentrated to give a crude product. 573 mg of pure product was obtained by column chromatography (94.8% yield).

Workup

  1. stirringThe mixture was stirred overnight at 25° C. before the volatiles
  2. customwere removed under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (20 mL)
  4. washwas washed with saturated sodium carbonate and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto give a crude product

Sources & evidence

ORD record
ord-537bf7508b6c42efbc970b7e61fbd5c3
Source dataset
uspto-grants-2015_06
Patent number
US09061060B2

Reaction notes

Loading…