Dimethyl Sulfoxide → 4-Bromonaphthalene-2-carbaldehyde

Temperature

-45 °C

Under a nitrogen atmosphere, an oxalyl chloride methylene chloride solution (2.0 M, 4.88 ml) was diluted with methylene chloride (40 ml), and dimethyl sulfoxide (0.9 ml, 12.7 mmol) was added dropwise thereto at −78° C. To this solution, a solution of (4-bromonaphthalene-2-yl)-methanol (1.15 g, 4.88 mmol) as synthesized according to a document [J. Med. Chem., 37, 2485 (1993)] in methylene chloride (10 ml) was added dropwise over 10 minutes. This reaction mixture was stirred at −78° C. for 15 minutes and −45° C. for one hour, and then triethylamine (4.0 ml, 29.3 mmol) was added dropwise thereto and stirred at 0° C. for 30 minutes. To the reaction solution, a saturated ammonium chloride aqueous solution was added and the resulting solution was extracted with methylene chloride. The organic layer was washed with water and a saturated sodium chloride aqueous solution, and dried with sodium sulfate. After filtration, the solvent was distilled under reduced pressure, and the obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:20)] to obtain the title compound (890 mg, 78%).

1. additionwas added dropwise
2. customat −78° C
3. additionwas added dropwise over 10 minutes
4. stirringstirred at 0° C. for 30 minutes
5. extractionthe resulting solution was extracted with methylene chloride
6. washThe organic layer was washed with water
7. dry with materiala saturated sodium chloride aqueous solution, and dried with sodium sulfate
8. filtrationAfter filtration
9. distillationthe solvent was distilled under reduced pressure
10. customthe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:20)]

ORD record

ord-18e6034387304741bbd97e86c968b6a2

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07943748B2