Methanol → HCID 18787032, compound

2-Bromo-6-prop-2-enyl-4-nitrophenol (5.8 g) was dissolved in dichloromethane (30 ml) and methanol (30 ml) and the resulting solution was cooled to -78° C. Ozone was bubbled through the solution until a faint blue coloration was observed and all starting material had reacted. The solution was purged with nitrogen, sodium borohydride (850 g) was added and the solution was allowed to come to room temperature. The solvent was evaporated and the residue was dispersed between ethyl acetate and HCl (1N). The ethyl acetate layer was washed with water, brine, dried (MgSO4) and concentrated. The residue was purified on silica using 2% methanol in dichloromethane as eluent to afford the title compound as a white solid (4 g). 1H NMR (360 MHz, CDCl3) δ 3.03 (2H, t, J=5.4 Hz), 4.06 (2H, t, J=5.5 Hz), 8.01 (1H, d, J=2.6 Hz), 8.35 (1H, d, J=2.6 Hz).

1. customOzone was bubbled through the solution until a faint blue coloration
2. customall starting material had reacted
3. customThe solution was purged with nitrogen, sodium borohydride (850 g)
4. additionwas added
5. customto come to room temperature
6. customThe solvent was evaporated
7. additionthe residue was dispersed between ethyl acetate and HCl (1N)
8. washThe ethyl acetate layer was washed with water, brine
9. dry with materialdried (MgSO4)
10. concentrationconcentrated
11. customThe residue was purified on silica using 2% methanol in dichloromethane as eluent

ORD record

ord-79f0a4a66ab1480eb902f81fde014a4a

Source dataset

uspto-grants-2000_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06060469