Iodine → 5-Iodo-2-(methoxymethyl)-4-methyl-1H-imidazole

Into a 100-mL round-bottom flask, was placed a solution of 2-(methoxymethyl)-4-methyl-1H-imidazole (compound 222.2, 1.9 g, 15.06 mmol) in sodium hydroxide aqueous solution (30 mL, 2M). This was followed by the addition of a solution of iodine (7.7 g, 30.34 mmol) in dichloromethane (30 mL). The reaction mixture was stirred for 1 h at room temperature. The aqueous phase was collected and the pH was adjusted to 4 with hydrogen chloride (2M). The reaction mixture was extracted with 4×30 mL of dichloromethane and the organic layers combined. The resulting mixture was washed with 2×20 mL of sodium sulfite (sat.) and 3×30 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. This resulted in 1.2 g (32%) of the title compound as a yellow solid.

1. customInto a 100-mL round-bottom flask, was placed
2. customThe aqueous phase was collected
3. extractionThe reaction mixture was extracted with 4×30 mL of dichloromethane
4. washThe resulting mixture was washed with 2×20 mL of sodium sulfite (sat.) and 3×30 mL of brine
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure

ORD record

ord-068943e911734acbac9f19ddd17c08bf

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2