Iodine → 2-Iodo-1-(methyloxy)-3-{[(methyloxy)methyl]oxy}benzene

Temperature

-70 °C

To a solution of 1-(methyloxy)-3-{[(methyloxy)methyl]oxy}benzene (Intermediate 1, 10 g, 59.5 mmol) in tetrahydrofurane (100 ml, SCRC) precooled to −78° C. was added dropwise BuLi (2.5 M in THF, 28.5 ml, 71.3 mmol, SCRC), maintaining the inner temperature lower than −70° C. After the addition was complete, the mixture was stirred at −70° C. for 2 hours and a solution of iodine (15.09 g, 59.5 mmol, SCRC) in THF (50 ml, SCRC) was added dropwise. The resulting mixture was stirred for 2 hours at room temperature and quenched with a saturated aqueous solution of ammonium chloride (100 ml). The mixture was extracted with ethyl acetate (3 times 300 ml, SCRC) and the combined organic layers were dried, evaporated and purified by silica gel chromatography with as eluents EtOAc: PE (1/100) to afford the title compound (16.2 g) as a yellow liquid.

1. customprecooled to −78° C.
2. additionAfter the addition
3. stirringThe resulting mixture was stirred for 2 hours at room temperature
4. customquenched with a saturated aqueous solution of ammonium chloride (100 ml)
5. extractionThe mixture was extracted with ethyl acetate (3 times 300 ml, SCRC)
6. customthe combined organic layers were dried
7. customevaporated
8. custompurified by silica gel chromatography with as eluents EtOAc

ORD record

ord-bfec453f74a9465da13ba5c1ab5b7272

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422272B2