Triethylamine → HCID 54429599, compound

Temperature

25 °C

A mixture of 2-fluorobenzoic acid (4.5 g, 32.14 mmol), oxalyl chloride (4.1 mL, 48.2 mL), DMF (2 drops) and methylene chloride (40 mL) was heated 2 hours at reflux. The reaction mixture was allowed to cool to 25° C., then stirred approximately 12 hours and concentrated. The residue was slowly added to a suspension of 2-bromoethylamine hydrobromide (5.7 g, 28 mmol), triethylamine (21 mL, 160 mmol) and benzene (200 mL). The mixture was heated 12 hours at reflux, allowed to cool to 25° C., stirred an additional 12 hours and diluted with water. The aqueous layer was separated and extracted with methylene chloride (2×50 mL). The combined extracts were dried (MgSO4) and concentrated. The residue was purified on silica gel by column chromatography eluting with hexanes/ethyl acetate (5:1) to give 2-fluoro-1-(4,5-dihydrooxazol-2-yl)benzene (1.96 g, 11.9 mmol).

1. temperaturewas heated 2 hours
2. temperatureat reflux
3. concentrationconcentrated
4. temperatureThe mixture was heated 12 hours
5. temperatureat reflux
6. temperatureto cool to 25° C.
7. stirringstirred an additional 12 hours
8. customThe aqueous layer was separated
9. extractionextracted with methylene chloride (2×50 mL)
10. dry with materialThe combined extracts were dried (MgSO4)
11. concentrationconcentrated
12. customThe residue was purified on silica gel by column chromatography
13. washeluting with hexanes/ethyl acetate (5:1)

ORD record

ord-0b9ff295e6b045a6b1169eaf9aa1aa6f

Source dataset

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05859014