Dibromomethane → HCID 10015501, compound

n-BuLi (2.6 M in hexane, 2.5 mL, 6.6 mmoL) was added dropwisely to a solution of diisopropylamine (0.93 mL, 6.6 mmol) in THF (20 mL) at −78° C. and stirred for 30 min at the same temperature. Hexamethylphosphoramide (4 mL) was added to the reaction mixture and stirred for 20 min at the same temperature. A solution of compound A122-1 (1.01 g, 6 mmol) in THF (5 mL) was added and stirred for 1 h at the same temperature. A solution of dibromomethane (2.1 mL, 30 mmol) was added to the reaction mixture and the mixture was allowed to warm to room temperature for 1.5 h. The reaction mixture was diluted hexane (80 mL) and AcOEt (20 mL). The collected organic layer washed with water, saturated NH4Cl aq., brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silicagel chromatography (10% EtOAc/hexane as eluent) to provide compound A122-2 (1.39 g, 89%) as a pale yellow oil.

1. stirringstirred for 20 min at the same temperature
2. stirringstirred for 1 h at the same temperature
3. washThe collected organic layer washed with water, saturated NH4Cl aq., brine
4. dry with materialdried over MgSO4
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by silicagel chromatography (10% EtOAc/hexane as eluent)
7. customto provide compound A122-2 (1.39 g, 89%) as a pale yellow oil

ORD record

ord-57bbb206983c45e78ea3765980f7499c

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365522B2