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

HRID 79090

反応式

HRID 79090 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9f7bf643af834bcf9eac33852c2667cc
出典データセット
uspto-grants-2014_09
特許番号
US08841483B2

関連ノート

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