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

HRID 60561ノート

反応式

HRID 60561 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-ff4cffabfd8144d49d757ba3c5c1f7c1
出典データセット
uspto-grants-2016_09
特許番号
US09440994B2

反応ノート

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