Hydrochloric Acid → 5-Methoxy-2-nitrophenol

Temperature

60 °C

Part A: 5-Fluoro-2-nitrophenol (5.00 g, 31.8 mmol) and methanol (120 mL) were combined and the mixture was treated with sodium methoxide (4.6 mL, 190.8 mmol, 25% w/w solution in MeOH). The reaction mixture was heated at 60° C. for 40 h. The mixture was transferred to a separatory funnel containing cold 1 N HCl and the aqueous layer was extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to afford 5-methoxy-2-nitrophenol (5.0 g, 93% yield) as a yellow solid: mp 93.0–94.0° C., 1H NMR (300 MHz, CDCl3): δ 11.05 (s, 1H), 8.03 (d, J=10.3 Hz, 1H), 6.55–6.51 (m, 2H), 3.89 (s, 3H).

1. customThe mixture was transferred to a separatory funnel
2. extractionthe aqueous layer was extracted with EtOAc (3×)
3. washThe combined organic layers were washed with brine
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-a7d543057a0d4cac9eebbfc553fc4004

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07205306B2