Triethylamine → 2-Bromo-N-isopropyl-N-(4-methoxyphenyl)acetamide

To a solution of isopropyl-(4-methoxy-phenyl)-amine (25.11 g) in dichloromethane (250 mL) was added triethylamine (15.38 g) with stirring at ambient temperature. The solution was cooled in an ice bath (<3° C.) and bromoacetyl bromide (30.68 g) dissolved in dichloromethane (100 mL) was added dropwise over a 45 minute period with stirring and cooling in an ice bath. The reaction mix was stirred overnight at ambient temperature, washed with 0.3N HCl (300 mL) and brine (300 mL), dried over sodium sulfate, filtered, and evaporated under reduced pressure to give a dark brown oil. The oil was filtered through a pad of silica gel (150 g) which was eluted with ethyl acetate/hexane (1:1, 900 mL) and the filtrate evaporated under reduced pressure to afford the title compound (41.05 g) as a brown oil which crystallized on standing.

1. additionwas added dropwise over a 45 minute period
2. stirringwith stirring
3. temperaturecooling in an ice bath
4. additionThe reaction mix
5. stirringwas stirred overnight at ambient temperature
6. washwashed with 0.3N HCl (300 mL) and brine (300 mL)
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. customevaporated under reduced pressure
10. customto give a dark brown oil
11. filtrationThe oil was filtered through a pad of silica gel (150 g) which
12. washwas eluted with ethyl acetate/hexane (1:1, 900 mL)
13. customthe filtrate evaporated under reduced pressure

ORD record

ord-683f94156b5e4ef6b40384c9d4141862

Source dataset

uspto-grants-1999_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05910495