Methanol → HCID 15027328, compound

Temperature

-78 °C

The product of Example 48A (3.21 g, 13.3 mmol) was dissolved in CH2Cl2 (30 mL), cooled to −78° C. and treated with BBr3 (8.31 g, 3.26 mmol). The resulting dark red solution was stirred at 25° C. for 4 min, then cooled to −78° C. Methanol (100 mL) was added slowly. The solution was concentrated in vacuo. Toluene was added to the crude and concentrated again. After adding more toluene, the solution was washed with water and concentrated in vacuo. The residue was dissolved in ether and extracted with NaOH (1.0 g) in water (8 mL). The aqueous layer was removed and stirred 15 minutes, then acidified with concentrated HCl. This mixture was extracted with toluene, dried (Na2SO4), filtered, concentrated in vacuo and the residue crystallized from ether and heptane (2:1) to provide the title compound (1.063 g, m.p. 122-125° C.).

1. temperaturecooled to −78° C
2. concentrationThe solution was concentrated in vacuo
3. additionToluene was added to the crude
4. concentrationconcentrated again
5. additionAfter adding more toluene
6. washthe solution was washed with water
7. concentrationconcentrated in vacuo
8. dissolutionThe residue was dissolved in ether
9. extractionextracted with NaOH (1.0 g) in water (8 mL)
10. customThe aqueous layer was removed
11. stirringstirred 15 minutes
12. extractionThis mixture was extracted with toluene
13. dry with materialdried (Na2SO4)
14. filtrationfiltered
15. concentrationconcentrated in vacuo
16. customthe residue crystallized from ether and heptane (2:1)

ORD record

ord-ca773c882f2d4ab2a5fa64f502f63666

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290444B2