Dimethylformamide → 4-bromo-1-methoxy-2-Naphthalenecarboxaldehyde

In a nitrogen stream, an n-butyllithium hexane solution (1.6 M, 56.9 ml, 91.1 mmol) was added dropwise to a solution of 2,4-dibromo-1-methoxy-naphthalene (30.3 g, 95.9 mmol) in THF (1,800 ml) at −78° C. and the reaction mixture was stirred at the same temperature for 30 minutes. To this mixture, N,N-dimethylformamide (8.9 ml, 115.1 mmol) was added at −78° C. The mixture was stirred at the same temperature for three hours, and then a saturated ammonium chloride aqueous solution was added thereto and the mixture was extracted with ether. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:8)] to obtain the title compound (3.85 g, 15%).

1. stirringThe mixture was stirred at the same temperature for three hours
2. extractionthe mixture was extracted with ether
3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
4. dry with materialdried (anhydrous magnesium sulfate)
5. distillationthe solvent was distilled under reduced pressure
6. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:8)]

ORD record

ord-d1582ed2dc19494f88b89f6228af3535

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07943748B2