Allyl bromide → HCID 86684751, compound

Temperature

0 °C

In a dry 3-necked flask flushed with argon containing a solution of 5-bromo-2-chloro-3-fluoro-pyridine (4.0 g, 19.05 mmol) at 0° C. was added isopropyl magnesium chloride lithium chloride complex (1.3 M THF solution, 24.76 mmol, 19.1 mL) over 10 minutes. After additional 10 min of stirring at 0° C., CuI (0.73 g, 3.81 mmol) was added and stirred for 10 min at 0° C. Then a solution of allyl bromide (38.1 mmol, 3.3 mL) in THF (4.0 mL) was added to the above mixture at 0° C. over a 10 min period. The resulting mixture was stirred for 1 h at 0° C., then quenched with 10% citric acid and extracted with ethyl acetate. The organic layers were separated, washed with brine, and concentrated. The obtained residue was chromatographed on silica gel eluted with hexane and 10% ethyl acetate in hexanes to afford 2.5 g (77%) of 2 as a colorless oil. 1HNMR (CDCl3) δ 3.41 (2 H, d, J=7.0 Hz) 5.18 (2 H, m), 5.92 (1 H, m), 7.33 (1 H, d, J=8.0 Hz), 8.06 (1 H, m); LC/MS (M+1) 173.

1. stirringstirred for 10 min at 0° C
2. stirringThe resulting mixture was stirred for 1 h at 0° C.
3. customquenched with 10% citric acid
4. extractionextracted with ethyl acetate
5. customThe organic layers were separated
6. washwashed with brine
7. concentrationconcentrated
8. customThe obtained residue was chromatographed on silica gel
9. washeluted with hexane and 10% ethyl acetate in hexanes

ORD record

ord-de16770f1b9342f6a73576e76edcd4c9

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921373B2