Sodium Iodide → HCID 18615568, compound

Temperature

74 °C

A 2L, 3 neck round bottom flask was equipped with an overhead stirrer, heating mantle, condenser, and nitrogen inlet. The flask was flushed with nitrogen and charged with acetonitrile (700 mL), followed by 5-bromo-2,3-dihydroxyethylbenzene (54.5 g, assumed to be 0.25 mol), then anhydrous cesium carbonate (121 g, 0.37 mol) and bromochloromethane (57 g, 0.44 mol). The mixture was stirred and heated to reflux (˜74° C.). At that point, sodium iodide (5 g, 0.03 mol) was added, and the mixture was boiled for 90 minutes. The mixture was then cooled and filtered with suction. The filter cake was rinsed with acetonitrile, then the solvent was removed under vacuum. The residue was treated with water (700 mL), and the mixture was extracted twice with 400 mL portions of hexane. The hexane was removed under vacuum, then the residue (˜36 g) was distilled under high vacuum. The distillate, collected at a head temperature of 84° C. (0.8 mm Hg) weighed 24 g (0.10 mol, 41% for the two steps). The product thus obtained has NMR characteristics consistent with the title compound and is greater than 95% pure by gas chromatography.

1. temperatureheating mantle, condenser, and nitrogen inlet
2. customThe flask was flushed with nitrogen
3. additioncharged with acetonitrile (700 mL)
4. temperatureheated
5. temperatureThe mixture was then cooled
6. filtrationfiltered with suction
7. washThe filter cake was rinsed with acetonitrile
8. customthe solvent was removed under vacuum
9. additionThe residue was treated with water (700 mL)
10. extractionthe mixture was extracted twice with 400 mL portions of hexane
11. customThe hexane was removed under vacuum
12. distillationthe residue (˜36 g) was distilled under high vacuum
13. distillationThe distillate, collected at a head temperature of 84° C. (0.8 mm Hg)
14. customThe product thus obtained

ORD record

ord-ace59039733f4e97a4ce07879843c6a4

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06252070B1