تفاعل #1994288

معادلة التفاعل

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

isopropylmagnesium chloride

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

diethyl ether

→

title compound

المردود 71.1%

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

المردود 71.1%

المذيبات

THF

THF

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto warm toward 0° C. for 1 hour
2. 2
   درجة الحرارةcooled to −10° C. again
3. 3
   درجة الحرارةto warm to ambient temperature
4. 4
   استخلاصextracted with 1N sodium hydroxide
5. 5
   استخلاصextracted with dichloromethane twice
6. 6
   أخرىdried
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated

الإجراء التجريبي

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).

المصدر