Dimethyl Sulfoxide → HCID 59470541, compound

To a flame dried 50 mL round bottom flask was added 3-bromo-4-hydroxybenzonitrile (1.0 g, 5.05 mmol) followed by 5 mL of dimethyl sulfoxide. Potassium iodide (4.2 mg, 0.025 mmol) and potassium carbonate (1.05 g, 7.58 mmol) were added. The flask was immersed in an oil bath at 85° C. and 1-bromo-2-fluoroethane (0.769 g, 0.45 mL, 6.06 mmol) was added. The reaction was stirred at this temperature for 1 h after which it was cooled to room temperature and diluted with water (10 mL). The resulting solution was extracted with dichloromethane (2×20 mL). The organic layer was then washed with water (3×20 mL) and brine, and dried over magnesium sulfate. The solution was filtered and concentrated in vacuo to obtain an oil which was purified by silica gel flash chromatography using dichloromethane. Product (1.13 g, 92%) was obtained as a colorless solid. 1H NMR (600 MHz, CDCl3): δ 7.83 (s, 1H), 7.57 (d of d, 1H, J=8.4, 1.8 Hz), 6.94 (d, 1H, J=8.4 Hz), 4.8 (t of d, 2H, J=49, 1.2 Hz), 4.35 (t of d, 2H, J=24, 1.2 Hz). 13C NMR (150 MHz, CDCl3): δ 158.5, 136.9, 132.9, 117.5, 113, 106, 81.5 (d, J=171 Hz), 68.5 (d, J=21 Hz). HRMS: Calc'd for C9H7BrFNO (M+H): 243.9767; Found: 243.9767.

1. customTo a flame dried 50 mL round bottom flask
2. customThe flask was immersed in an oil bath at 85° C.
3. extractionThe resulting solution was extracted with dichloromethane (2×20 mL)
4. washThe organic layer was then washed with water (3×20 mL) and brine
5. dry with materialdried over magnesium sulfate
6. filtrationThe solution was filtered
7. concentrationconcentrated in vacuo
8. customto obtain an oil which
9. customwas purified by silica gel flash chromatography

ORD record

ord-dd52d21df75d4617ada24f9dd9370627

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08491868B2