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

HRID 909770Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 909770
[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

Komponenten

6

Edukt 4

HCID 8000Boron trifluoride etherateHCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 46205463(3-Bromophenyl)(4-ethoxyphenyl)methanol

Produkt 1

HCID 462057871-bromo-3-(4-ethoxybenzyl)benzeneAusbeute 76,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-25045e6a96e7421283a24bae1ab88e66
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017792B2

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