Allyl Alcohol → 3-(4-Bromo-2-methylphenyl)propanal

HRID 734834

反応式

HRID 734834 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([CH3:9])[CH:3]=1.[CH2:10]([OH:13])[CH:11]=[CH2:12].C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:12][CH2:11][CH:10]=[O:13])=[C:4]([CH3:9])[CH:3]=1

参加物

8

反応物 3

HCID 7858Allyl AlcoholHCID 516892Sodium BicarbonateHCID 27246015-Bromo-2-iodotoluene

生成物 1

HCID 822879023-(4-Bromo-2-methylphenyl)propanal

試薬・触媒・溶媒 4

HCID 70681Tetrabutylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
45 °C

実験手順

A mixture of 1.00 g (3.39 mmol) of 4-bromo-1-iodo-2-methylbenzene, 0.58 g (10.00 mmol) of allyl alcohol, 0.69 g (8.20 mmol) of sodium bicarbonate, 0.92 g (3.30 mmol) of tetrabutylammonium chloride, and 22 mg (0.10 mmol) of palladium (II) acetate in 5 mL of DMF were stirred for 16 hours at 45° C. under argon. The reaction mixture was diluted with EtOAc, and the organic phase was washed with water, dried over magnesium sulfate, and evaporated down in vacuo. The residue was purified by column chromatography (silica gel, PE/EtOAc 4:1). Yield: 0.60 (78% of theoretical); C10H11BrO (M=227.098); calc.: molpeak (M+H)+: 226/228 (Br); found: molpeak (M+H)+: 226/228 (Br); Rf value: 0.45 (silica gel, PE/EtOAc 4:1).

後処理

  1. washthe organic phase was washed with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated down in vacuo
  4. customThe residue was purified by column chromatography (silica gel, PE/EtOAc 4:1)

出典と根拠

ORDレコード
ord-40fa67226683452dbd5c8ffd0ab090eb
出典データセット
uspto-grants-2009_09
特許番号
US07592358B2

関連ノート

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