Cyclobutanone → HCID 86698600, compound

Temperature

-40 °C

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 (1.3 M 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 (1.3 M 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.

1. stirringThe reaction mixture was stirred at −40° C. for an additional 20 minutes
2. temperatureThe reaction mixture was warmed to room temperature
3. stirringstirred at room temperature for 16 hours
4. customThe reaction mixture was quenched with water
5. extractionextracted with ethyl acetate (3×240 mL)
6. dry with materialThe combined organic layers were dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-b6c6f3c4738f4b7a94faafeefc22d8c4

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394285B2