4-Bromophenol → 4-(2-(4-Bromophenoxy)ethyl)morpholine

温度

110 °C

To a mixture of 2-(morpholin-4-yl)ethanol (197 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 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 with ethyl acetate (50 mL), washed with 2M aqueous NaOH (3×15 mL) and brine (2×20 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to give a residue, which was purified by flash chromatography on silica gel to give 4-[2-(4-bromophenoxy)ethyl]morpholine (480 mg, 100%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.35 (d, 2H), δ 6.70 (d, 2H), 4.07 (t, 2H), 3.74-3.71 (m, 4H), 2.78 (t, 2H), 2.57-2.55 (m, 4H).

1. customThe 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 aqueous NaOH (3×15 mL) and brine (2×20 mL)
7. dry with materialThe organic layer was dried over sodium sulfate
8. concentrationconcentrated in vacuo
9. customto give a residue, which
10. customwas purified by flash chromatography on silica gel

ORDレコード

ord-80b5b4fac1b04ee4b7cb85b3c463f2fa

出典データセット

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08889730B2