Tributylvinyltin → HCID 68433557, compound

Temperature

90 °C

A solution of methyl 2-chloro-5-iodo-3-nitrobenzoate (3 g, 8.8 mmol) and vinyl tributyltin (3.6 g, 11.4 mmol) in DMF (50 mL) was degassed with argon. PdCl2/(PPh3)2 (308 mg, 0.44 mmol) was added, the reaction vessel was sealed under argon and the reaction mixture was stirred at 90° C. for 16 h. The reaction mixture was cooled to RT and treated with aqueous KF (1.5 g in 20 mL water) for 2 h30. The mixture was diluted with water and EtOAc filtered on cellite. The organic layer was separated, washed with aq LiCl (×3), dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography (120 g silica gel, 0 to 20% EtOAc in hexane) to give methyl 2-chloro-3-nitro-5-vinylbenzoate as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.94 (d, J=2 Hz, 1H), 7.83 (d, J=2 Hz, 1H), 6.69 (dd, J=17.4 Hz, 10.8 Hz, 1H), 5.89 (d, J=17.4 Hz, 1H), 5.52 (d, J=10.8 Hz, 1H), 3.99 (s, 3H).

1. customthe reaction vessel was sealed under argon
2. temperatureThe reaction mixture was cooled to RT
3. filtrationfiltered on cellite
4. customThe organic layer was separated
5. washwashed with aq LiCl (×3)
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated in vacuo
8. custompurified by flash chromatography (120 g silica gel, 0 to 20% EtOAc in hexane)

ORD record

ord-40258507286d4d56adc8a40b7b018ad5

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07678783B2