Reaction #70218

Reaction equation

NH4Cl

iodomethane

aldehyde

2-Bromo-5-isopropoxy-4-methoxybenzaldehyde

→

title compound 37

Yield 99.2%

1-(2-Bromo-5-isopropoxy-4-methoxyphenyl)ethanol

Yield 99.2%

Solvents

Et2O

Et2O

Et2O

Et2O

Conditions

Workup

1. 1
   workup.ADDITIONthen treated
2. 2
   Temperatureto warm to 18° C. at which temperature it
3. 3
   workup.STIRRINGwas stirred for a further 1 h
4. 4
   WashThe separated organic phase was washed with H2O (1×20 mL)
5. 5
   Dryingthen dried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated under reduced pressure

Procedure

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.

Source