Sodium Hydroxide → HCID 39834387, compound

Temperature

60 °C

A mixture of 3-iodoanisole (0.6 mL, 5 mmol), 1-methyl-2-(tributylstannyl)-1H-imidazole (Bull. Chem. Soc. Jpn. 1986, 59, 677, 2.5 g, 6 mmol), and dichlorobis(triphenylphosphine)palladoim(II) (421 mg, 0.6 mmol) in N,N-dimethylformamide (10 mL) was stirred at 60° C. for 8 h under nitrogen atmosphere. The reaction mixture was poured into 2 N sodium hydroxide aqueous solution (10 mL) and the basic mixture was extracted with ethyl acetate (30 mL×6). The combined organic extracts were washed with brine (10 mL×2) and dried (sodium sulfate). After removal of solvent, the residue was purified by column chromatography on silica gel eluting with dichloromethane/methanol (20/1) to afford 724 mg (77%) of the title compound as pale orange oil: 1H-NMR (CDCl3) δ 7.39–7.33 (1H, m), 7.22–7.16 (2H, m), 7.13–7.12 (1H, m), 6.97–6.94 (2H, m), 3.86 (3H, s), 3.76 (3H, s); MS (ESI) m/z 189 (M+H)+.

1. extractionthe basic mixture was extracted with ethyl acetate (30 mL×6)
2. washThe combined organic extracts were washed with brine (10 mL×2)
3. dry with materialdried (sodium sulfate)
4. customAfter removal of solvent
5. customthe residue was purified by column chromatography on silica gel eluting with dichloromethane/methanol (20/1)

ORD record

ord-265ddc7d5a644de0810c02a7a12c9176

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07238714B2