Boron trifluoride → HCID 58385808, compound

HRID 1038347Notes

Reaction equation

HRID 1038347 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=1)=O.C([SiH](CC)CC)C.B(F)(F)F>ClCCl.C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[CH2:9][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH3:18])=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 6356Boron trifluorideHCID 12052TriethylsilaneHCID 58385804HCID 58385804, compound

Product 1

HCID 58385808HCID 58385808, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
47.5 °C

Procedure

A solution of (2-bromo-5-iodo-phenyl)-(4-ethyl-phenyl)-methanone (32 g) and triethylsilane (50 mL) in dichloromethane (30 mL) and acetonitrile (100 mL) is cooled in an ice-bath. Then, boron trifluoride diethyletherate (20 mL) is added dropwise over 5 min. The cooling bath is removed and the solution is heated to 45-50° C. and stirred at this temperature for 4 h. After cooling to ambient temperature, 4 M aqueous KOH solution is added and the resulting mixture is extracted with ethyl acetate. The combined organic phases are washed with 2 M potassium hydroxide solution and brine and then dried (sodium sulphate). After the solvent is evaporated, the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:0->9:1).

Workup

  1. customThe cooling bath is removed
  2. temperatureAfter cooling to ambient temperature
  3. addition4 M aqueous KOH solution is added
  4. extractionthe resulting mixture is extracted with ethyl acetate
  5. washThe combined organic phases are washed with 2 M potassium hydroxide solution and brine
  6. dry with materialdried (sodium sulphate)
  7. customAfter the solvent is evaporated
  8. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:0->9:1)

Sources & evidence

ORD record
ord-583230832da74400bff1c178c632a252
Source dataset
uspto-grants-2013_10
Patent number
US08551957B2

Reaction notes

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