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

HRID 1849981Notes

Reaction equation

HRID 1849981 reaction equation
B(F)(F)F.CCOCC.[Br:10][C:11]1[CH:12]=[CH:13][C:14]([Cl:28])=[C:15]([C:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH3:27])=[CH:21][CH:20]=2)=O)[CH:16]=1.[SiH](CC)(CC)CC.[OH-].[K+]>C(Cl)Cl.CC#N>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([Cl:28])=[C:15]([CH2:17][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH3:27])=[CH:21][CH:20]=2)[CH:16]=1

Participants

7

Reactant 4

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 14797Potassium HydroxideHCID 10020105(5-Bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone

Product 1

HCID 99964494-Bromo-1-chloro-2-(4-ethoxy-benzyl)-benzeneYield 156.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

At −20° C., BF3.Et2O (0.75 mL) was added slowly into a solution of (5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone (2 g) and Et3SiH (2 mL) in dry DCM (5 mL) and CH3CN (10 mL), then the mixture was stirred at room temperature for overnight. 7M KOH was slowly added into the mixture, and then the mixture was extracted with DCM, the organic phases were combined, dried over Na2SO4 and concentrated to obtain the crude product. The crude product was purified by silica-gel column chromatography (PE/EA=10/1) to obtain 3 g of 4-bromo-1-chloro-2-(4-ethoxybenzyl)benzene.

Workup

  1. extractionthe mixture was extracted with DCM
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto obtain the crude product
  5. customThe crude product was purified by silica-gel column chromatography (PE/EA=10/1)

Sources & evidence

ORD record
ord-a36a350bd8944be2909a88b9645e0c58
Source dataset
uspto-grants-2015_02
Patent number
US08957033B2

Reaction notes

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