Boron trifluoride etherate → 5-Bromo-2-chloro-1-(4-ethoxybenzyl)-3-methoxybenzene

HRID 2206712Notes

Reaction equation

HRID 2206712 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:20][CH3:21])[C:5]([Cl:19])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)=O)[CH:7]=1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.CC#N>[Br:1][C:2]1[CH:3]=[C:4]([O:20][CH3:21])[C:5]([Cl:19])=[C:6]([CH2:8][C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH3:18])=[CH:14][CH:15]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 71076739(5-Bromo-2-chloro-3-methoxyphenyl)(4-ethoxyphenyl)methanone

Product 1

HCID 710769175-Bromo-2-chloro-1-(4-ethoxybenzyl)-3-methoxybenzeneYield 87%

Reagents, catalysts & solvents 1

HCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

To a solution of methanone 73 (7.0 g, 18.94 mmol) in CH2Cl2/CH3CN (60 mL/60 mL) were added triethylsilane (9.1 mL, 56.81 mmol) and boron trifluoride diethyl etherate (7.0 mL, 56.81 mmol) at 0° C. The mixture was warmed up to room temperature slowly and stirred at room temperature for 15 hours. To the mixture was added aq. saturated K2CO3 solution (80 mL) slowly and extracted with EtOAc (100 mL×2). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the desired product 74 (5.7 g, 87%).

Workup

  1. extractionextracted with EtOAc (100 mL×2)
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f77ef672111d4fe3aec42a6462ffb41c
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

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