Diethyl Ether → HCID 59126908, compound

Temperature

-10 °C

1-Bromo-4-chloro-2,5-difluorobenzene (1.11 g, 4.9 mmol) was dissolved in tetrahydrofuran (THF; 15 mL) and cooled to −10° C. A 2.0M solution of isopropyl-magnesium chloride (2.7 mL, 5.4 mmol) in THF was added dropwise via syringe. The reaction mixture was stirred at −10° C. for 1 h, allowed to warm toward 0° C. for 1 h, then cooled again to −10° C. A solution of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.0 g, 5.4 mmol) in THF (1.0 mL) was then added dropwise and the reaction mixture was allowed to warm to ambient temperature. The reaction mixture was then added to diethyl ether and extracted with 1N sodium hydroxide twice. 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 (0.97 g, 72.3% yield) that was used without further purification: 1H NMR (CDCl3) δ 7.45 (dd, 1H), 7.09 dd, 1H), 1.36 (s, 12H).

1. temperatureto warm toward 0° C. for 1 h
2. temperaturecooled again to −10° C
3. temperatureto warm to ambient temperature
4. extractionextracted with 1N sodium hydroxide twice
5. extractionextracted with dichloromethane twice
6. customdried
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-111417bca82b4a28bf5d1e9e6c7d10fc

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268753B2