Pyridine, hydrofluoride (1:1) → HCID 90389310, compound

Temperature

0 °C

A PFA plastic round bottom flask was charged with a solution of hydrogen fluoride pyridine (70 wt % HF, 100 ml, 1150 mmol). The solution was cooled to 0° C. and 4-bromo-2-iodo-6-methylaniline (9.2 g, 29.5 mmol, Organic Letters 2009, 11, 249-251) was added portion wise. After 15 minutes, sodium nitrite (1.032 ml, 32.4 mmol) was added and the reaction mixture was stirred at 0° C. for additional 15 minutes. The reaction mixture was allowed to warm to room temperature and stirred for 15 minutes, followed by heating at 90° C. for 3 hour. The reaction mixture was then cooled to room temperature and quenched with water and diethyl ether. The organic layer was separated, washed with brine and dried over magnesium sulfate. The filtrate was concentrated under reduced pressure. The crude material was purified via silica gel chromatography eluting with hexanes to afford the title compound (8.45 g, 26.8 mmol, 91% yield) as a brown solid. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 2.29 (s, 3H) 7.27-7.34 (m, 1H) 7.64-7.75 (m, 1H)

1. temperatureto warm to room temperature
2. stirringstirred for 15 minutes
3. temperatureby heating at 90° C. for 3 hour
4. temperatureThe reaction mixture was then cooled to room temperature
5. customquenched with water and diethyl ether
6. customThe organic layer was separated
7. washwashed with brine
8. dry with materialdried over magnesium sulfate
9. concentrationThe filtrate was concentrated under reduced pressure
10. customThe crude material was purified via silica gel chromatography
11. washeluting with hexanes

ORD record

ord-6d363247401d4a58b213c4ecc0c10538

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085576B2