Dimethyl Sulfoxide → 4-Bromo-5-methylpicolinaldehyde

A solution of dimethyl sulfoxide (0.85 mL, 12.02 mmol) in DCM (10 mL) was added dropwise over 5 minutes to a solution of oxalyl chloride (0.47 mL, 5.51 mmol) in DCM (20 mL) at −78° C. under an atmosphere of N2 (gas evolved). Stirring was continued for 10 minutes. To this solution was added (4-bromo-5-methyl-2-pyridyl)methanol [CAS: 820224-83-7](1.01 g, 5.01 mmol) in DCM (2 mL) dropwise over a period of 10 minutes. Stirring was then continued for a further 10 minutes. Triethylamine (3.13 mL, 22.54 mmol) was added dropwise and stirring continued for 5 minutes, before allowing the reaction to warm to room temperature. Water was added and the phases were separated by passing over a hydrophobic frit. The organic phase was evaporated to yield a dark brown solid which was dried under vacuum overnight (795 mg). This was purified by column chromatography on silica gel (0-100% EtOAc in isohexane) to yield 4-bromo-5-methyl-pyridine-2-carbaldehyde (D21) (619 mg, 3.0945 mmol, 61.8% yield) as an orange crystalline solid;

1. stirringStirring
2. waitwas then continued for a further 10 minutes
3. stirringstirring
4. waitcontinued for 5 minutes
5. customthe reaction
6. customthe phases were separated
7. customThe organic phase was evaporated
8. customto yield a dark brown solid which
9. customwas dried under vacuum overnight (795 mg)
10. customThis was purified by column chromatography on silica gel (0-100% EtOAc in isohexane)

ORD record

ord-2793f04076724782abdedcd1cf56a4ac

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376436B2