Reacción #46217

Ecuación de reacción

6-bromo-2,2,4,4-tetrafluoro-4H-benzo[1,3]dioxine

→

2,2,4,4-tetrafluoro-4H-benzo[1,3]dioxine-6-carboxylic acid methyl ester

Rendimiento 169.8%

Disolventes

MeOH

MeCN

Et3N

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe cooled reaction mixture
2. 2
   Filtraciónwas filtered
3. 3
   Concentraciónthe filtrate was concentrated
4. 4
   OtroThe residue was purified by silica gel column (Petroleum Ether)

Procedimiento

A suspension of 6-bromo-2,2,4,4-tetrafluoro-4H-benzo[1,3]dioxine (4.75 g, 16.6 mmol) and Pd(PPh3)4 (950 mg, 8.23 mmol) in MeOH (20 mL), MeCN (30 mL) and Et3N (10 mL) was stirred under carbon monoxide atmosphere (55 psi) at 75° C. (oil bath temperature) overnight. The cooled reaction mixture was filtered and the filtrate was concentrated. The residue was purified by silica gel column (Petroleum Ether) to give 2,2,4,4-tetrafluoro-4H-benzo[1,3]dioxine-6-carboxylic acid methyl ester (3.75 g, 85%). 1H NMR (CDCl3, 300 MHz) δ 8.34 (s, 1H), 8.26 (dd, J=2.1, 8.7 Hz, 1H), 7.22 (d, J=8.7 Hz, 1H), 3.96 (s, 3H).

Fuente