Boron trifluoride etherate → 1-(4-Ethylbenzyl)-5-bromo-2-chloro-3-methoxybenzene

HRID 576334Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 576334
[Br:1][C:2]1[CH:3]=[C:4]([O:19][CH3:20])[C:5]([Cl:18])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=2)=O)[CH:7]=1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:16]([C:13]1[CH:14]=[CH:15][C:10]([CH2:8][C:6]2[CH:7]=[C:2]([Br:1])[CH:3]=[C:4]([O:19][CH3:20])[C:5]=2[Cl:18])=[CH:11][CH:12]=1)[CH3:17]

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 71110682(5-Bromo-2-chloro-3-methoxyphenyl)(4-ethylphenyl)methanone

Produkt 1

HCID 710770511-(4-Ethylbenzyl)-5-bromo-2-chloro-3-methoxybenzeneAusbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of compound 61 (4.45 g, 12.6 mmol) in CH2Cl2 (80 mL) was added dropwise triethylsilane (6.00 mL, 37.8 mmol) and boron trifluoride diethyl etherate (4.67 mL, 37.8 mmol) at 0° C. under an atmosphere of nitrogen. After being stirred for 5 hours at room temperature, the mixture was quenched with aq. saturated K2CO3 solution (30 mL) and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford the product 62 (2.40 g, 56%) as colorless oil.

Aufarbeitung

  1. customthe mixture was quenched with aq. saturated K2CO3 solution (30 mL)
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-30339ba797054e6bba0d5dcbfcb86040
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034921B2

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