3-Chlorophenol → 4-(3-Chlorophenoxy)-2-methyl-1-nitrobenzene

Temperature

110 °C

To a suspension of 3-chloro-phenol (1.65 g, 12.89 mmol) in DMF (10 mL), was added KOH (1.45 g, 25.78 mmol) and the mixture heated at 110° C. for 30 min. The mixture was cooled to 25° C. and 4-fluoro-2-methyl-1-nitro-benzene (0.5 g, 3.22 mmol) was added. This mixture was then heated to 130° C. for 12 h. The reaction mixture was treated with 10% NaOH solution and extracted with EtOAc (3×25 mL). The organic phase was washed with brine (3×5 mL), dried over sodium sulfate and concentrated. The residue was purified by column chromatography (silica, 0.5% EtOAc in hexanes) to afford 4-(3-chloro-phenoxy)-2-methyl-1-nitro-benzene (400 mg, 47%). MS (M+H)+=263; 1H NMR (CDCl3) δ: 8.05 (d, J=7.1 Hz, 1H), 7.33 (t, J=6.0 Hz, 1H), 7.20 (d, J=5.3 Hz, 1H), 7.06 (s, 1H), 7.03-6.85 (m, 3H), 2.59 (s, 3H).

1. temperatureThe mixture was cooled to 25° C.
2. temperatureThis mixture was then heated to 130° C. for 12 h
3. extractionextracted with EtOAc (3×25 mL)
4. washThe organic phase was washed with brine (3×5 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated
7. customThe residue was purified by column chromatography (silica, 0.5% EtOAc in hexanes)

ORD record

ord-9f16e3346a5d4c2381ce962c8ad18422

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658646B2