4-Bromophenol → 1369534-96-2

Temperature

110 °C

To oxetan-3-ol (112 mg, 1.5 mmol) in THF (5 mL) was added 4-bromophenol (200 mg, 1.16 mmol), polymeric triphenylphosphine (0.5 g, 1.5 mmol) and DIAD (305 mg, 1.5 mmol). The reaction mixture was degassed with nitrogen for 2 min and stirred at 110° C. for 17 hours. The cooled reaction mixture was filtered and the filtrate was concentrated in vacuo to give a residue, which was dissolved in ethyl acetate (50 mL) and washed with 2M NaOH (3×15 mL) and brine (2×20 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo to give a residue, which was purified by flash chromatography on silica gel eluting with EtOAc/petroleum ether (1:10) to give 3-(4-bromophenoxy)oxetane (140 mg, 53%) as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 7.37 (d, 2H), δ 6.55 (d, 2H), 5.19-5.13 (m, 1H), 4.97-4.94 (m, 2H), 4.76-4.73 (m, 2H).

1. customThe reaction mixture was degassed with nitrogen for 2 min
2. customThe cooled reaction mixture
3. filtrationwas filtered
4. concentrationthe filtrate was concentrated in vacuo
5. customto give a residue, which
6. washwashed with 2M NaOH (3×15 mL) and brine (2×20 mL)
7. dry with materialThe organic layer was dried over Na2SO4
8. concentrationconcentrated in vacuo
9. customto give a residue, which
10. customwas purified by flash chromatography on silica gel eluting with EtOAc/petroleum ether (1:10)

ORD record

ord-9346f1b1b1ca44ddafa9ce9aba6b7215

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08889730B2