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

HRID 2234735Notes

Reaction equation

HRID 2234735 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 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 resulting mixture is stirred for 2 h. Then the organic phase is separated off and the aqueous phase is extracted another three times with diisopropylether. The combined organic phases are washed twice with aqueous 2 M potassium hydroxide solution and once with brine and then dried over sodium sulfate. After the solvent has been removed the residue is washed in ethanol, separated again 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. stirringthe resulting mixture is stirred for 2 h
  6. customThen the organic phase is separated off
  7. extractionthe aqueous phase is extracted another three times with diisopropylether
  8. washThe combined organic phases are washed twice with aqueous 2 M potassium hydroxide solution and once with brine
  9. dry with materialdried over sodium sulfate
  10. customAfter the solvent has been removed the residue
  11. washis washed in ethanol
  12. customseparated again
  13. customdried at 60° C.

Sources & evidence

ORD record
ord-f37169ba5c594b1aad950b781f3c3ebb
Source dataset
uspto-grants-2010_05
Patent number
US07713938B2

Reaction notes

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