1-Bromotridecane → HCID 21225990, compound

Temperature

0 °C

n-BuLi (1.6M, 32 mL) was added dropwise to a 0° C. solution of N-t-butylethanesulfonamide (4.0 g, 24 mmoles) in anhydrous THF (80 mL) under dry N2. The solution was stirred for 30 minutes at 0° C then warmed to room temperature for 30 minutes. It was then cooled back to 0° C. and a solution of 1-bromotridecane (6.4 mL, 25 mmoles) in 10 mL anhydrous THF (distilled from Na-Ph2CO) was added dropwise. The solution was allowed to warm to room temperature overnight, quenched by addition of 1N HCl (60 mL), and partitioned between ethyl acetate and brine. The organic layer was dried, filtered, and concentrated to an oil, which was dissolved in 40 mL of CF3CO2H and stirred overnight at room temperature. It was then concentrated and the solid residue recrystallized from iPr2O to afford 4.8 g (68%) of 2-pentadecylsulfonamide as a light brown (almond) powder.

1. temperaturethen warmed to room temperature for 30 minutes
2. temperatureIt was then cooled back to 0° C.
3. temperatureto warm to room temperature overnight
4. customquenched by addition of 1N HCl (60 mL)
5. custompartitioned between ethyl acetate and brine
6. customThe organic layer was dried
7. filtrationfiltered
8. concentrationconcentrated to an oil, which
9. dissolutionwas dissolved in 40 mL of CF3CO2H
10. stirringstirred overnight at room temperature
11. concentrationIt was then concentrated
12. customthe solid residue recrystallized from iPr2O

ORD record

ord-daec1658c8044f7a9840d6af70e3a88f

Source dataset

uspto-grants-1993_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05254589