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

HRID 79090

반응식

HRID 79090 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 110971531-(4-Tert-butyl-2-bromophenyl)ethanone수율 24.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9f7bf643af834bcf9eac33852c2667cc
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841483B2

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