Stannane, tributyl(1-methylethenyl)- → 2-Chloro-4-isopropenyl-benzoic acid methyl ester

HRID 60561노트

반응식

HRID 60561 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][C:5]=1[Cl:11].[C:13]([Sn](CCCC)(CCCC)CCCC)([CH3:15])=[CH2:14]>C1COCC1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([C:13]([CH3:15])=[CH2:14])=[CH:6][C:5]=1[Cl:11]

참가 물질

4

반응물 2

HCID 10871254Stannane, tributyl(1-methylethenyl)-HCID 22058730Methyl 4-Bromo-2-chlorobenzoate

생성물 1

HCID 669274782-Chloro-4-isopropenyl-benzoic acid methyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

To a solution of 4-bromo-2-chlorobenzoic acid methyl ester (500 mg, 2 mmol) in THF (15 mL) was added isopropenyltributylstannane (700 mg, 2.1 mmol) and PdCl2(dppf)-2-DCM (165 mg, 0.2 mmol). The solution was heated to 60° C. for 12 hours. The crude reaction mixture was then concentrated down and taken up in 20 mL EtOAc and 100 mL concentrated KF solution. The reaction stirred at room temperature for 3 hours, filtered through a pad of celite and concentrated down. The residual oil was subjected to flash chromatography (Isco Companion, 40 g SiO2 cartridge, solid loaded SiO2, neat heptanes to EtOAc gradient) to give 2-chloro-4-isopropenyl-benzoic acid methyl ester as a yellow oil. Amount obtained: 230.6 mg (55%). LCMS (M/Z): 211 (M+H).

후처리

  1. customThe crude reaction mixture
  2. concentrationwas then concentrated down
  3. filtrationfiltered through a pad of celite
  4. concentrationconcentrated down

출처 및 근거

ORD 기록
ord-ff4cffabfd8144d49d757ba3c5c1f7c1
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440994B2

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