1,2-Dibromoethane → HCID 18630171, compound

Temperature

-78 °C

To a solution of the compound of Example 201 (0.79 g, 2.2 mmol) and TMEDA (0.44 mL, 2.9 mmol) in THF (20 mL) at -78° C. was added a solution of 0.86 M s-BuLi in cyclohexane (3.3 mL, 2.9 mmol). The reaction was stirred at -78° C. for 30 min and 1,2-dibromoethane (0.26 mL, 3.0 mmol) was added. The reaction was stirred for 15 min at -78° C. and was quenched with sat NaHCO3. The mixture was extracted with ether, washed with brine, dried (MgSO4) and concentrated to afford a yellow oil. This oil was dissolved in a mixture of acetone (30 mL) and 6 N HCl (15 mL) and was stirred overnight. The mixture was concentrated, extracted with ether, the organic layers washed with brine, dried (MgSO4) and concentrated to afford the title compound as a clear oil. The crude product was purified by RC (ethyl acetate/hexanes) and was recrystallized from pentane (-78° C.) to afford 76 mg of a white solid (10% yield). m.p. 105°-106° C.

1. stirringThe reaction was stirred for 15 min at -78° C.
2. customwas quenched with sat NaHCO3
3. extractionThe mixture was extracted with ether
4. washwashed with brine
5. dry with materialdried (MgSO4)
6. concentrationconcentrated
7. customto afford a yellow oil
8. stirringwas stirred overnight
9. concentrationThe mixture was concentrated
10. extractionextracted with ether
11. washthe organic layers washed with brine
12. dry with materialdried (MgSO4)
13. concentrationconcentrated

ORD record

ord-86ee4aa08f79454d9f10b0da9270c7de

Source dataset

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

USRE036562