4-Bromoaniline → Propanamide, N-(4-bromophenyl)-2-methyl-

In a 500 mL three-neck flask were put 16 g (90 mmol) of 4-bromoaniline, 11 g (108 mmol) of triethylamine, and 250 mL of tetrahydrofuran (THF), and the mixed solution was stirred. To this mixed solution, a mixed solution of 9.6 g (90 mmol) of isobutyryl chloride and 50 mL of THF was added dropwise under cooling with ice, and the mixture was stirred at room temperature for 12 hours. After the stirring, this mixture was dissolved in chloroform, and washed with water and a saturated aqueous solution of sodium hydrogen carbonate. After the washing, anhydrous magnesium sulfate was added to the organic layer for drying. The resulting mixture was subjected to gravity filtration, and the filtrate was concentrated to give a solid. This solid was washed with hexane to give 18 g of a white solid of N-(4-bromophenyl)isobutyramide in a yield of 82%. The reaction scheme of Step 1 is shown in (b-1) below.

1. customIn a 500 mL three-neck flask were put
2. temperatureunder cooling with ice
3. washwashed with water
4. additionAfter the washing, anhydrous magnesium sulfate was added to the organic layer
5. customfor drying
6. filtrationThe resulting mixture was subjected to gravity filtration
7. concentrationthe filtrate was concentrated
8. customto give a solid
9. washThis solid was washed with hexane

ORD record

ord-1688d90724074d10ba8878e6439db78c

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09155158B2