Boron trifluoride etherate → 1-Benzyloxy-2-bromo-5-methyl-4-[4-[2-(methoxymethoxy)ethyl]benzyl]benzene

HRID 1009873Notes

Reaction equation

HRID 1009873 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([Br:15])=[CH:13][C:12]([CH:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][O:26][CH2:27][O:28][CH3:29])=[CH:20][CH:19]=2)O)=[C:11]([CH3:30])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SiH](CC)(CC)CC.B(F)(F)F.CCOCC.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH3:30])[C:12]([CH2:16][C:18]2[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][O:26][CH2:27][O:28][CH3:29])=[CH:22][CH:23]=2)=[CH:13][C:14]=1[Br:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 67304665[4-(Benzyloxy)-5-bromo-2-methylphenyl][4-[2-(methoxymethoxy)ethyl]phenyl]methanol

Product 1

HCID 673042011-Benzyloxy-2-bromo-5-methyl-4-[4-[2-(methoxymethoxy)ethyl]benzyl]benzeneYield 68%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Then to a chloroform solution (1 L) of [4-(benzyloxy)-5-bromo-2-methylphenyl][4-[2-(methoxymethoxy)ethyl]phenyl]methanol (102 g) cooled in ice were added Et3SiH (46.7 mL, 0.293 mol) and BF3.Et2O (29.7 mL, 0.243 mol), and the mixture was stirred for 15 minutes at the same temperature. To the reaction solution cooled in ice was added a saturated sodium bicarbonate aqueous solution and warmed to room temperature. The resulting mixture was extracted with ethyl acetate, washed with brine, and then the organic layer was dried with anhydrous magnesium sulfate. The drying agent was filtered off, and the solvent was evaporated under reduced pressure. Thus obtained residue was purified with NH type silica gel column chromatography (hexane:ethyl acetate=19:1 to 9:1) to obtain the title compound (60 g, 68%) as a pale yellow oily compound.

Workup

  1. temperatureTo the reaction solution cooled in ice
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe solvent was evaporated under reduced pressure
  7. customThus obtained residue was purified with NH type silica gel column chromatography (hexane:ethyl acetate=19:1 to 9:1)

Sources & evidence

ORD record
ord-28065decb6494f56a4c7e6366b9c8f66
Source dataset
uspto-grants-2011_07
Patent number
US07973012B2

Reaction notes

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