Reserpine → 4-Bromo-2-chloro-1-phenoxybenzene

A mixture of 4-bromo-2-chlorophenol (2.07 g, 10 mmol), phenyl boronic acid (3.66 g, 30 mmol), copper(II) acetate (2.0 g, 1.1 mmol) and 4A powdered molecular sieves (20 g) in dichloromethane (100 mL) was treated with triethylamine (5.0 g, 50 mmol) then stirred at ambient temperature for 5 days. The mixture was diluted with heptane (100 mL), then filtered through a bed of celite. The filtrate was concentrated under reduced pressure to remove dichloromethane. The mixture was extracted with IN hydrochloric acid, 15 wt % aqueous sodium hydroxide, brine and then dried over magnesium sulfate. The mixture was filtered and the filtrate concentrated under reduced pressure to provide (1.27 g, 45%): 1H NMR (DMSO-d6, 400 MHz) δ 7.87(s, 1H), 7.55(d, 1H), 7.40(t, 2H), 7.17(t, 1H), 6.99(m, 3H); MS MH+283; RP-HPLC (Hypersil HS, 5 μm, 100 A 4.6×250 mm; 25%-100% acetonitrile—0.05 M ammonium acetate over 10 min, 1 m/min) tr 14.42min.

1. filtrationfiltered through a bed of celite
2. concentrationThe filtrate was concentrated under reduced pressure
3. customto remove dichloromethane
4. extractionThe mixture was extracted with IN hydrochloric acid, 15 wt % aqueous sodium hydroxide, brine
5. dry with materialdried over magnesium sulfate
6. filtrationThe mixture was filtered
7. concentrationthe filtrate concentrated under reduced pressure
8. customto provide (1.27 g, 45%)
9. customtr 14.42min.

ORD-Eintrag

ord-11c4d1aba29d43eb826cea2fa995c699

Quelldatensatz

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06713474B2