Boron trifluoride etherate → 4-Bromo-1-chloro-2-(4-methoxybenzyl)benzene

HRID 2246486Notes

Reaction equation

HRID 2246486 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:18])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=O)[CH:7]=1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC.[OH-].[K+]>ClCCl.C(#N)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:18])=[C:6]([CH2:8][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:7]=1

Participants

8

Reactant 4

HCID 8000Boron trifluoride etherate2×HCID 12052Triethylsilane2×HCID 14797Potassium HydroxideHCID 22328608(5-Bromo-2-chloro-phenyl)-(4-ethoxy-phenyl)-methanone

Product 1

HCID 223285944-Bromo-1-chloro-2-(4-methoxybenzyl)benzene

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
47.5 °C

Procedure

A solution of 86.2 g (5-bromo-2-chloro-phenyl)-(4-methoxy-phenyl)-methanone and 101.5 mL triethylsilane in 75 mL dichloromethane and 150 mL acetonitrile is cooled to 10° C. Then with stirring 50.8 mL of boron trifluoride etherate are added so that the temperature does not exceed 20° C. The solution is stirred for 14 h at ambient temperature, before another 9 mL triethylsilane and 4.4 mL boron trifluoride etherate are added. The solution is stirred for a further 3 h period at 45-50° C. and then cooled to ambient temperature. A solution of 28 g potassium hydroxide in 70 mL water is added, and the resultant mixture is stirred for 2 h. The organic phase is separated and the aqueous phase is extracted another three times with diisopropylether. The combined organic phases are washed twice with 2 M potassium hydroxide solution and once with brine and then dried over sodium sulfate. After the solvent is evaporated, the residue is washed with ethanol and dried at 60° C.

Workup

  1. additionare added so that the temperature
  2. customdoes not exceed 20° C
  3. additionare added
  4. temperaturecooled to ambient temperature
  5. customThe organic phase is separated
  6. extractionthe aqueous phase is extracted another three times with diisopropylether
  7. washThe combined organic phases are washed twice with 2 M potassium hydroxide solution and once with brine
  8. dry with materialdried over sodium sulfate
  9. customAfter the solvent is evaporated
  10. washthe residue is washed with ethanol
  11. customdried at 60° C.

Sources & evidence

ORD record
ord-e1e8350b63aa4a83b3436c29823da9fa
Source dataset
uspto-grants-2010_03
Patent number
US07687469B2

Reaction notes

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