Tributylvinyltin → HCID 58373146, 화합물

HRID 60556

반응식

HRID 60556 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 58373146HCID 58373146, 화합물

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 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).

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-f457df4c287242d89060fb6b3d20cb8d
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440994B2

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