Acetyl chloride → 1-(4-Tert-butyl-2-bromophenyl)ethanone

HRID 79090

Reaktionsgleichung

Reaktionsgleichung von HRID 79090
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[Br:9][C:10]1[CH:11]=[C:12]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=[CH:14][CH:15]=1>C(Cl)Cl>[C:16]([C:12]1[CH:13]=[CH:14][C:15]([C:5](=[O:7])[CH3:6])=[C:10]([Br:9])[CH:11]=1)([CH3:19])([CH3:18])[CH3:17]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 3437981-Bromo-3-tert-butylbenzeneHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 110971531-(4-Tert-butyl-2-bromophenyl)ethanoneAusbeute 24,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

Aluminum chloride (8.0 g, 60 mmol) was stirred in CH2Cl2 (200 mL), and acetyl chloride (8.5 mL, 120 mmol) was slowly added, producing a homogeneous solution. A solution of 3-bromo tert-butyl benzene (11 g, 50 mmol) in CH2Cl2 (20 mL) was slowly added, and the reaction was stirred at room temperature 16 h. After being diluted with CH2Cl2, the reaction was washed with water, saturated aqueous NaHCO3, and water. The organic solution was dried over Na2SO4 and concentrated under vacuum. Purification by silica gel chromatography (0%-50% CH2Cl2-hexanes) afforded 1-(4-tert-butyl-2-bromophenyl)ethanone (3.1 g, 24% yield) as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.61 (d, J=1.8 Hz, 1H), 7.46 (d, J=8.1 Hz, 1H), 7.37 (dd, J=8.1, 1.8 Hz, 1H), 2.63 (s, 3H), 1.32 (s, 9H) ppm.

Aufarbeitung

  1. customproducing a homogeneous solution
  2. washthe reaction was washed with water, saturated aqueous NaHCO3, and water
  3. dry with materialThe organic solution was dried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customPurification by silica gel chromatography (0%-50% CH2Cl2-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-9f7bf643af834bcf9eac33852c2667cc
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841483B2

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