Dimethyl Sulfoxide → HCID 23657662, compound

Temperature

50 °C

To a flame dried, 1 L, three necked round bottom flask (1 L) equipped with a temperature controller, a mechanical stirrer, a condenser and a N2 inlet was charged 3-bromo-5-fluorophenol (57.3 g, 300 mmol), 1,2-dibromotetrafluoroethane (156.0 g, 600 mmol), dry DMSO (300 mL) and Cs2CO3 (146.6 g, 450 mmol) under N2. The reaction mixture was heated to 50° C. for 5 h. After cooling to rt, water (300 mL) and hexane (300 mL) were added. The resulting mixture was stirred at rt for 30 min. The organic phase was separated and the aqueous layer was extracted with hexane (300 mL). The combined organic extracts were washed with water (500 mL), sat. NaCl (500 mL), dried over MgSO4, filtered and concentrated in vacuo to give 1-bromo-3-(2-bromo-1,1,2,2-tetrafluoroethoxy)-5-fluorobenzene (104.2 g, 94% yield) containing 5% of 1-bromo-3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)benzene (5.2 g). 1-Bromo-3-(2-bromo-1,1,2,2-tetrafluoroethoxy)-5-fluorobenzene: 1H NMR (300 MHz, CDCl3) δ 6.91-6.94 (m, 1H), 7.18-7.23 (m, 2H).

1. customTo a flame dried
2. custom1 L, three necked round bottom flask (1 L) equipped with a temperature controller, a mechanical stirrer, a condenser and a N2 inlet
3. temperatureAfter cooling to rt
4. customThe organic phase was separated
5. extractionthe aqueous layer was extracted with hexane (300 mL)
6. washThe combined organic extracts were washed with water (500 mL), sat. NaCl (500 mL)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-ccff9adbc02648f28a2ac6e47592ddf9

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08304403B2