تفاعل #425436

معادلة التفاعل

isopropyl magnesium chloride

cyclobutanone

1-bromo-2-fluoro-4-iodobenzene

isopropyl magnesium chloride

lithium chloride

lithium chloride

→

title compound

المردود 91.0%

1-(4-bromo-3-fluorophenyl)cyclobutanol

المردود 91.0%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe reaction mixture was stirred at −40° C. for an additional 20 minutes
2. 2
   درجة الحرارةThe reaction mixture was warmed to room temperature
3. 3
   workup.STIRRINGstirred at room temperature for 16 hours
4. 4
   أخرىThe reaction mixture was quenched with water
5. 5
   استخلاصextracted with ethyl acetate (3×240 mL)
6. 6
   تجفيفThe combined organic layers were dried over sodium sulfate
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated in vacuo

الإجراء التجريبي

To 1-bromo-2-fluoro-4-iodobenzene (2390 mg, 7.90 mmol) in tetrahydrofuran (20 mL) at −40° C. was added isopropyl magnesium chloride.lithium chloride (1.3M in THF, 6.4 mL, 5.1 mmol) dropwise. The reaction mixture was stirred at −40° C. for 10 minutes, and treated with additional isopropyl magnesium chloride.lithium chloride (1.3M in THF, 1 mL, 1.3 mmol). The reaction mixture was stirred at −40° C. for an additional 20 minutes and then treated with cyclobutanone (624 mg, 8.72 mmol) dropwise at −40° C. The reaction mixture was warmed to room temperature, and stirred at room temperature for 16 hours. The reaction mixture was quenched with water and extracted with ethyl acetate (3×240 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound (1.7 g, 91%) as an oil.

المصدر