Methyl iodide → 1-(2-Bromo-5-isopropoxy-4-methoxyphenyl)ethanol

Temperature

0 °C

A mixture of Mg turnings (231 mg, 9.51 g·atom) in dry Et2O (3.0 mL) was stirred at 0° C. under a nitrogen atmosphere then treated, dropwise, with a solution of iodomethane (680 μL, 10.9 mmol) in dry Et2O (2.0 mL). After 0.5 h a solution of aldehyde 36 (1.00 g, 3.66 mmol) in dry Et2O (10 mL) was added, dropwise, to the reaction mixture that was then allowed to warm to 18° C. at which temperature it was stirred for a further 1 h. After this time NH4Cl (15 mL of a 20% w/v aqueous solution) then Et2O (20 mL) were added to the reaction mixture. The separated organic phase was washed with H2O (1×20 mL) then dried (MgSO4), filtered and concentrated under reduced pressure to afford the title compound 37 (1.05 g, 99%) as an orange oil.

1. additionthen treated
2. temperatureto warm to 18° C. at which temperature it
3. stirringwas stirred for a further 1 h
4. washThe separated organic phase was washed with H2O (1×20 mL)
5. dry with materialthen dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure

ORD record

ord-cfc0d04a7ad44679ae041b23872c8b19

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08536157B2