Tributylvinyltin → HCID 58373146、化合物

HRID 60556ノート

反応式

HRID 60556 の反応式
C[O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][C:5]=1[Cl:11].[CH2:13]([Sn](CCCC)(CCCC)C=C)[CH2:14]CC>C1COCC1>[Cl:11][C:5]1[CH:6]=[C:7]([CH:13]=[CH2:14])[CH:8]=[CH:9][C:4]=1[C:3]([OH:2])=[O:12]

参加物

4

反応物 2

HCID 81998TributylvinyltinHCID 22058730Methyl 4-Bromo-2-chlorobenzoate

生成物 1

HCID 58373146HCID 58373146、化合物

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 tributyl(vinyl)tin (620 μl, 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-vinylbenzoic acid as a yellow oil. Amount obtained: 235 mg (60%). LCMS (M/Z): 197 (M+H). 1H NMR (Chloroform-d) δ: 3.93 (s, 3 H) 5.42 (d, J=10.9 Hz, 1 H) 5.86 (d, J=17.6 Hz, 1 H) 6.66 (dd, J=17.6, 10.7 Hz, 1 H) 7.28-7.35 (m, 1 H) 7.43-7.50 (m, 1 H) 7.82 (d, J=8.0 Hz, 1 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-f457df4c287242d89060fb6b3d20cb8d
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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