Oxazole → 2-(4-Fluorophenyl)-1,3-oxazole

A solution of 1-fluoro-4-iodobenzene (1 g, 0.0144 mmol) in DMF (15 mL) was purged with argon, and oxazole (6.4 g/3.3 mL, 0.02898 mmol), copper iodide (5.5 g, 0.02898 mmol) and palladium (II) acetate (0.15 g, 0.000724 mmol) was added. The reaction mixture was purged with argon for 5 min and refluxed under argon for 12 h. The solution was cooled to room temperature and diluted with ice cold water (100 mL). The reaction mixture was extracted with ethyl acetate (200 mL) and filtered through Celite® reagent. The organic solvent was dried with sodium sulfate, filtered and the solvent was removed under reduced pressure to obtain crude product. The crude product was purified by Biotage IsoleraOne® column using a 25 g column (7% ethyl acetate in hexane) to give 2-(4-fluorophenyl)oxazole (0.6 g, 26%) as yellow liquid. 1H NMR (400 MHz, DMSO-d6): δ 8.19 (s, 1H), 8.03-7.99 (m, 2H), 7.34 (t, 3H); LC-MS m/z calculated for [M+H]+ 164.05, found 164.1.

1. additionwas added
2. customThe reaction mixture was purged with argon for 5 min
3. temperaturerefluxed under argon for 12 h
4. additiondiluted with ice cold water (100 mL)
5. extractionThe reaction mixture was extracted with ethyl acetate (200 mL)
6. filtrationfiltered through Celite® reagent
7. dry with materialThe organic solvent was dried with sodium sulfate
8. filtrationfiltered
9. customthe solvent was removed under reduced pressure
10. customto obtain crude product
11. customThe crude product was purified by Biotage IsoleraOne® column

ORD record

ord-5595d12198584f8c932e830c2c6b3c2e

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809372B2