3-Iodophenol → HCID 66223408, compound

Temperature

130 °C

3-Iodophenol (5.35 g, 24.3 mmol) was added to a suspension of NaH (1.46 g, 36.5 mmol, 60% in mineral oil) in anhydrous DMF (30 mL) at 0° C. After hydrogen evolution had ceased, 15-crown-5 (0.535 g, 2.43 mmol) and 2-bromo-1,1-dimethoxyethane (7.1 g, 42 mmol) were added. The resulting mixture was heated at 130° C. for 3 h, cooled to room temperature, poured into water (200 mL), and extracted with Et2O (3×150 mL). The combined organic layers were washed with water (100 mL) and brine (100 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified on a silica gel column using EtOAc in petroleum ether (1:50) to afford the title compound (6.36 g, 85%). 1H NMR (DMSO-d6, 400 MHz): δ 7.32 (s, 1H), 7.30-7.26 (m, 1H), 7.07 (t, 1H), 7.00-6.94 (m, 1H), 4.66 (t, 2H), 3.98 (d, 1H), 3.33 (s, 6H).

1. temperaturecooled to room temperature
2. extractionextracted with Et2O (3×150 mL)
3. washThe combined organic layers were washed with water (100 mL) and brine (100 mL)
4. dry with materialdried over Na2SO4
5. concentrationconcentrated in vacuo
6. customThe residue was purified on a silica gel column

ORD record

ord-bd25b54fdcd649dd9e84fdbdea73caf9

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09399646B2