Pentane → HCID 57705717, compound

Temperature

-78 °C

To a −78° C. solution of 2-bromo-1-butoxy-4-methoxybenzene 4.1 (250 mg, 965 μmol) in THF (8.0 mL) was added tert-butyllithium, 1.7 M solution in pentane (1248 μL, 2122 μmol) dropwise under a blanket of nitrogen. The pale yellow solution was stirred for 0.5 h at −78° C. before dropwise addition of neat trimethyl borate (175 μL, 1544 μmol) at the same temperature. The resulting mixture was stirred for 1 hour at −78° C., warmed to 25° C., and stirred for an additional hour. The reaction was quenched with saturated aqueous ammonium chloride and concentrated. The resulting residue was suspended in water/acetic acid (pH=3) and extracted with DCM. The combined organic layers were washed with saturated aqueous sodium bicarbonate and brine, dried (MgSO4), and concentrated to afford a light brown solid. The product was purified by trituration with hexane to afford 2-butoxy-5-methoxyphenylboronic acid 4.2 (67.2 mg, 31.1% yield) as a white powder.

1. temperaturewarmed to 25° C.
2. stirringstirred for an additional hour
3. customThe reaction was quenched with saturated aqueous ammonium chloride
4. concentrationconcentrated
5. extractionextracted with DCM
6. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate and brine
7. dry with materialdried (MgSO4)
8. concentrationconcentrated
9. customto afford a light brown solid
10. customThe product was purified by trituration with hexane

ORD record

ord-4b9366b032df4e7da01a76f28b301963

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08030354B2