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

HRID 500322Notes

Reaction equation

HRID 500322 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. 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 at 45 to 50° C. and then cooled to ambient temperature. A solution of 28 g potassium hydroxide in 70 mL of water is added, and the resultant mixture is stirred for 2 h. Then the organic phase is separated, and the aqueous phase is extracted 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 removed, the residue is washed with ethanol and dried at 60° C.

Workup

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

Sources & evidence

ORD record
ord-12fd880a19aa4874a89a1eda5be596bd
Source dataset
uspto-grants-2010_08
Patent number
US07772191B2

Reaction notes

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