Ethylene Glycol → HCID 68618823, compound

Temperature

80 °C

To a mixture of 2-fluoro-4-iodoaniline (1 g, 4.14 mmol), copper iodide (304 mg, 0.21 mmol) and potassium phosphate (1.75 g, 8.27 mmol) in ethylene glycol (465 μl, 8.27 mmol) and isopropanol (4 mL) in a bomb flask was added azetidine (304 mg, 5.17 mmol). The flask was sealed and heated to 80° C. for 24 hours. The reaction mixture was dissolved in ethyl acetate (50 mL), washed with water (3×50 mL), brine (50 mL), and the brine layer back extracted with ethyl acetate (2×50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to a brown oil. The oil was purified by chromatography over silica gel eluted with 40% v/v ethyl acetate in hexanes. The product containing fractions were combined and concentrated to give 4-azetidin-1-yl-2-fluoro-phenylamine as an orange oil (555 mg, 81% yield).

1. customThe flask was sealed
2. washwashed with water (3×50 mL), brine (50 mL)
3. extractionthe brine layer back extracted with ethyl acetate (2×50 mL)
4. dry with materialThe combined organic extracts were dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo to a brown oil
7. customThe oil was purified by chromatography over silica gel
8. washeluted with 40% v/v ethyl acetate in hexanes
9. additionThe product containing fractions
10. concentrationconcentrated

ORD record

ord-9872ef8f04314c79be82978671bae91b

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07612212B2