Acetonitrile → 1-Iodo-4-[(2-methylbut-3-yn-2-yl)oxy]benzene

To a solution of 4-iodophenol (6.05 g, 27.5 mmol), in anhydrous acetonitrile (25 mL) cooled to 0° C. was added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 4.50 mL, 30.1 mmol). The solution was stirred for 10 minutes then the title B compound (2.56 g, 25 mmol) was added followed by copper(II) chloride dihydrate (5.1 mg, 0.030 mmol). The reaction mixture was stirred at 0° C. for five hours then concentrated in vacuo. The residue was partitioned between 200 mL of toluene and 40 mL of 1M aq HCl solution. The organic layer was washed with two-40 mL portions of 1M aq HCl solution, two-40 mL portions of 1M aq NaOH solution, brine then dried (magnesium sulfate) and concentrated in vacuo to give a pale yellow liquid. The crude material was purified by bulb-to-bulb distillation (100° C., 0.1 mm) to afford the title compound as a colorless liquid (5.65 g, 19.7 mmol, 79%).

1. stirringThe reaction mixture was stirred at 0° C. for five hours
2. concentrationthen concentrated in vacuo
3. customThe residue was partitioned between 200 mL of toluene and 40 mL of 1M aq HCl solution
4. washThe organic layer was washed with two-40 mL portions of 1M aq HCl solution, two-40 mL portions of 1M aq NaOH solution, brine
5. dry with materialthen dried (magnesium sulfate)
6. concentrationconcentrated in vacuo
7. customto give a pale yellow liquid
8. distillationThe crude material was purified by bulb-to-bulb distillation (100° C., 0.1 mm)

ORD record

ord-d1b0fcc4092d4956a68c07fc4ab4b9d6

Source dataset

uspto-grants-1997_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05612323