Tetrahydrofuran → HCID 22138728, compound

An oven-dried, two liter, three-necked, round-bottomed flask was charged with 4-acetyl-phenylboronic acid (20 grams, 0.152 mole). While stirring, 175 ml of THF were added to the reaction mixture, followed by 700 ml of chloroform. To the resulting solution was added 5 ml of glacial acetic acid. A chloroform solution of bromine (prepared by dissolving 7 ml of bromine in 30 ml of chloroform) was added slowly to the reaction mixture at about 5° C. After the completion of the addition of bromine, the reaction mixture was allowed to warm to room temperature and stirred at room temperature for 16 hours. The solvent was removed by rotary evaporation and the residue was dissolved in 1 liter of ethyl acetate. The resulting solution was extracted with deionized water (3×200 ml) and brine (2×100 ml). The organic layer was dried over anhydrous sodium sulfate for 1 hour. The solution was then filtered and concentrated to about ⅓ of its volume. The resulting solution was kept in a freezer to crystallize the product. The solid was filtered to give an off white solid. Yield=16 grams.

1. stirringstirred at room temperature for 16 hours
2. customThe solvent was removed by rotary evaporation
3. dissolutionthe residue was dissolved in 1 liter of ethyl acetate
4. extractionThe resulting solution was extracted with deionized water (3×200 ml) and brine (2×100 ml)
5. dry with materialThe organic layer was dried over anhydrous sodium sulfate for 1 hour
6. filtrationThe solution was then filtered
7. concentrationconcentrated to about ⅓ of its volume
8. customto crystallize the product
9. filtrationThe solid was filtered
10. customto give an off white solid

ORD record

ord-c6c4396c0d224d5fa51865bf7055e734

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07456156B2