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

HRID 909805Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 909805
[SiH](CC)(CC)CC.B(F)(F)F.C[CH2:13][O:14]CC.[Br:17][C:18]1[CH:19]=[CH:20][C:21]([Cl:37])=[C:22]([C:26]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH3:36])=[CH:30][CH:29]=2)=O)[C:23]=1OC.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl.C(#N)C>[Br:17][C:18]1[C:19]([O:14][CH3:13])=[CH:20][C:21]([Cl:37])=[C:22]([CH2:26][C:28]2[CH:29]=[CH:30][C:31]([O:34][CH2:35][CH3:36])=[CH:32][CH:33]=2)[CH:23]=1

Komponenten

6

Edukt 4

HCID 8000Boron trifluoride etherateHCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 67069096(5-Bromo-2-chloro-6-methoxyphenyl)(4-ethoxyphenyl)methanone

Produkt 1

HCID 670691051-Bromo-4-chloro-5-(4-ethoxybenzyl)-2-methoxybenzeneAusbeute 102,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22555007Acetonitrile chloroformLösungsmittel

Versuchsvorschrift

Then, Et3SiH (1.62 mL, 10.1 mmol) and BF3.Et2O (0.772 mL, 6.09 mmol) were added sequentially to a chloroform-acetonitrile (1:1; 16 mL) solution of (5-bromo-2-chloro-6-methoxyphenyl)(4-ethoxyphenyl)methanone (1.50 g, 4.06 mmol) at −5° C. The reaction mixture was warmed to room temperature and stirred for 16 hours. 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=20:1) to obtain a colorless oily title compound (1.48 g, 99%).

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=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-3a6c97e11d9e43959280864211ab560c
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017792B2

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