Tributylvinyltin → HCID 58373146, compound

HRID 60556

Reaction equation

HRID 60556 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

HCID 58373146HCID 58373146, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-f457df4c287242d89060fb6b3d20cb8d
Source dataset
uspto-grants-2016_09
Patent number
US09440994B2

Linked notes

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