Boron trifluoride etherate → 1-bromo-3-(4-ethoxybenzyl)benzene

HRID 909770Notes

Reaction equation

HRID 909770 reaction equation
[SiH](CC)(CC)CC.B(F)(F)F.CCOCC.[Br:17][C:18]1[CH:19]=[C:20]([CH:24]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH3:34])=[CH:28][CH:27]=2)O)[CH:21]=[CH:22][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH3:34])=[CH:28][CH:27]=2)[CH:19]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 46205463HCID 46205463, compound

Product 1

HCID 462057871-bromo-3-(4-ethoxybenzyl)benzeneYield 76.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Then, Et3SiH (4.09 mL, 0.0256 mol) and BF3.Et2O (1.47 mL, 0.0116 mol) were added sequentially to a chloroform (22 mL) solution of (3-bromophenyl)(4-ethoxyphenyl)methanol (3.92 g, 0.0128 mol) at −60° C. After stirred for one hour, the reaction solution was warmed to room temperature. After the reaction mixture was added with a saturated sodium carbonate aqueous solution and extracted with chloroform, the organic layer was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=50:1) to obtain a colorless oily title compound (2.84 g, 76%).

Workup

  1. extractionextracted with chloroform
  2. washthe organic layer was washed with brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationAfter the desiccant was filtered off
  5. customthe residue obtained
  6. customby evaporating the solvent under reduced pressure
  7. customwas purified by silica gel column chromatography (hexane:ethyl acetate=50:1)

Sources & evidence

ORD record
ord-25045e6a96e7421283a24bae1ab88e66
Source dataset
uspto-grants-2011_09
Patent number
US08017792B2

Reaction notes

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