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

HRID 734834노트

반응식

HRID 734834 반응식
[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

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
45 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-40fa67226683452dbd5c8ffd0ab090eb
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592358B2

반응 노트

불러오는 중…