Reacción #1994288

Ecuación de reacción

2-isopropoxy-4,4,5,5-tetramethyl[1,3,2]dioxaborolane

isopropylmagnesium chloride

1-Bromo-4,5-dichloro-2-fluorobenzene

diethyl ether

→

title compound

Rendimiento 71.1%

2-(4,5-Dichloro-2-fluorophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Rendimiento 71.1%

Disolventes

THF

THF

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm toward 0° C. for 1 hour
2. 2
   Temperaturacooled to −10° C. again
3. 3
   Temperaturato warm to ambient temperature
4. 4
   Extracciónextracted with 1N sodium hydroxide
5. 5
   Extracciónextracted with dichloromethane twice
6. 6
   Otrodried
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated

Procedimiento

1-Bromo-4,5-dichloro-2-fluorobenzene (1.0 g, 4.11 mmol) was dissolved in tetrahydrofuran (THF; 20 mL) and cooled to −10° C. A 2.0M solution of isopropylmagnesium chloride (2.3 mL, 4.6 mmol) in THF was added dropwise via a syringe. The reaction mixture was stirred at −10° C. for 1 hour, allowed to warm toward 0° C. for 1 hour, then cooled to −10° C. again. A solution of 2-isopropoxy-4,4,5,5-tetramethyl[1,3,2]dioxaborolane (0.85 g, 4.56 mmol) in THF (1.0 mL) was then added dropwise and the reaction was allowed to warm to ambient temperature. The reaction mixture was then added to diethyl ether and extracted with 1N sodium hydroxide. The aqueous phases were combined, acidified to pH 3 with concentrated HCl, and extracted with dichloromethane twice. The organic phases were combined, dried, filtered and concentrated to give the title compound (0.85 g, 71% yield) that was used without further purification: 1H NMR (CDCl3): δ 7.73 (d, 1H), 7.12 (d, 1H), 1.3 (s, 12H).

Fuente