Tert-Butylamine → 4-Bromomethyl-N-t-butyl-benzenesulfonamide

Temperature

0 °C

t-Butyl amine (5.9 mL, 56 mmol, 1.0 eq) and DIPEA (9.7 mL, 56 mmol, 1.0 eq) were added to 350 ml DCM. The solution was cooled to 0° C. and a solution of 4-bromomethylbenzenesulfonyl chloride (15.1 g, 56 mmol, 1.0 eq) in 100 mL DCM was added drop-wise via an addition funnel. The mixture was then slowly warmed to room temperature and stirred for 3 hours. The mixture was concentrated under reduced pressure and the residue was dissolved into 350 mL EtOAc. The organic was washed with 1N aq. HCl, saturated bicarbonate, water, saturated aqueous NaCl, dried over MgSO4, and filtered. The filtrate was concentrated to yield intermediate (2a) (13.6 g).

1. temperatureThe mixture was then slowly warmed to room temperature
2. concentrationThe mixture was concentrated under reduced pressure
3. dissolutionthe residue was dissolved into 350 mL EtOAc
4. washThe organic was washed with 1N aq. HCl, saturated bicarbonate, water, saturated aqueous NaCl
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationThe filtrate was concentrated

ORD record

ord-35b46c2751c74809b27bca03cb4e3b30

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501798B2