反应详情

A mixture of 4-bromobenzoic acid (200 g, 1 mol) and thionyl chloride (300 mL) was refluxed for 3 hours. The mixture was concentrated in vacuo to remove excessive thionyl chloride, and then azeotroped with toluene (3×). The crude residue was dissolved in CH2Cl2 (2 L) and cooled in ice-water bath. To the resulting solution was added dropwise a mixture of triethylamine (330 mL, 2.38 mol) and diisopropylamine (168 mL, 1.19 mol) over 1 hour. The solution was allowed to stir overnight, and then washed with 1N HCl, followed by brine. The organic layer was dried over MgSO4, filtered, and concentrated to afford 4-bromo-N,N-diisopropylbenzamide. LRMS calc'd for (C13H18BrNO) [M+H]+, 284; found 284.

1. temperaturewas refluxed for 3 hours
2. concentrationThe mixture was concentrated in vacuo
3. customto remove excessive thionyl chloride
4. customazeotroped with toluene (3×)
5. dissolutionThe crude residue was dissolved in CH2Cl2 (2 L)
6. temperaturecooled in ice-water bath
7. additionTo the resulting solution was added dropwise
8. washwashed with 1N HCl
9. dry with materialThe organic layer was dried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated