Triethylamine → HCID 54429599, compound

A mixture of 2-fluorobenzoic acid (4.5 g, 32.14 mmol) and oxalyl chloride (4.1 mL, 48.2 mL) in 2 drops of DMF and 40 mL of methylene chloride was heated at reflux for 2 hours. The mixture was allowed to cool to room temperature and stirred for approximately 12 hours and then the solvents were removed by rotary evaporation. The residue was slowly added to a suspension of 2-bromoethylamine hydrobromide (5.7 g, 28 mmol) and triethylamine (21 mL, 160 mmol) in 200 mL of benzene. The mixture was heated at reflux for 12 hours, allowed to cool to room temperature and then stirred for an additional 12 hours. The mixture was quenched with water and 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. temperatureat reflux for 2 hours
3. customthe solvents were removed by rotary evaporation
4. temperatureThe mixture was heated
5. temperatureat reflux for 12 hours
6. temperatureto cool to room temperature
7. stirringstirred for an additional 12 hours
8. customThe mixture was quenched with water
9. customthe aqueous layer was separated
10. extractionextracted with methylene chloride (2×50 mL)
11. dry with materialThe combined extracts were dried (MgSO4)
12. concentrationconcentrated
13. customThe residue was purified on silica gel by column chromatography
14. washeluting with hexanes/ethyl acetate (5:1)

ORD record

ord-1f719d512db74bdc89712918749eda29

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05688795