Potassium Iodide → HCID 60991563, compound

Temperature

100 °C

To a sealed tube containing a clear, slightly yellow solution of 3-chloroaniline (2.5 g, 19.60 mmol) and methyl 2-bromopropanoate (3.93 g, 23.52 mmol) in DMF (39.2 mL) was added potassium iodide (0.325 g, 1.960 mmol) and potassium carbonate (4.06 g, 29.4 mmol). The vessel was sealed with a Teflon screw cap possessing an o-ring. The resulting suspension was warmed to 100° C. After 5 h, the resulting dark brown reaction mixture was stopped and cooled to rt. The reaction was filtered to remove the solid, rinsing with EtOAc. The filtrate was partitioned between EtOAc and water and the layers were separated. The aqueous layer was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to give a brown liquid weighing 6.30 g. Purification by normal phase chromatography gave the desired product (1.04 g, 25%) as a clear, yellow oil. MS (ESI) m/z: 214.0 (M+H)+.

1. customscrew cap
2. temperaturecooled to rt
3. filtrationThe reaction was filtered
4. customto remove the solid
5. washrinsing with EtOAc
6. customThe filtrate was partitioned between EtOAc and water
7. customthe layers were separated
8. extractionThe aqueous layer was extracted with EtOAc (2×)
9. washThe combined organic layers were washed with brine
10. dry with materialdried over sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated
13. customto give a brown liquid
14. customPurification by normal phase chromatography

ORD record

ord-f39ae6e82f344443883c0f10a77bfc44

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901115B2