3-Bromo-4-methylpyridine-2-carbaldehyde → 1-(3-Bromo-4-methylpyridin-2-yl)ethanol

Temperature

-15 °C

Methylmagnesium chloride (3.0 mol/L) in THF (0.17 mL, 0.525 mmol) was added dropwise to a solution of 3-bromo-4-methyl-pyridine-2-carbaldehyde (100 mg, 0.50 mmol) in THF (2 mL) cooled at −15° C. After 5 min, the reaction was quenched with a few drops of saturated aqueous ammonium chloride solution. The reaction mixture was diluted with ethyl acetate (25 mL) and washed with water (5 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to provide the title compound as a yellow oil (100 mg, 92%), which was used in subsequent steps without further purification.

1. customthe reaction was quenched with a few drops of saturated aqueous ammonium chloride solution
2. additionThe reaction mixture was diluted with ethyl acetate (25 mL)
3. washwashed with water (5 mL)
4. customThe organic layer was separated
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-40ba4459b953430f80391996aa2385d2

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206175B2