Aniline → 2-Bromo-N-phenylacetamide

To a stirred solution of aniline (7.40 mmol) in methylene chloride (25 mL) at −50° C. was added successively N,N-diisopropylethylamine (1.58 mL, 8.14 mmol, 1.1 eq) and bromoacetyl bromide (0.72 mL, 7.40 mmol, 1 eq) such that the temperature did not exceed −40° C. On completion of the addition, the cooling bath was removed, and the reaction mixture was allowed to warm to room temperature. After stirring for a further 30 minutes, the mixture was diluted with ether (70 mL) and poured into 1 N sodium bisulfate solution. The phases were separated, and the upper layer was washed successively with water and brine. The organic phase was dried (Na2SO4) and the solvent evaporated to half volume, at which point the product crystallized. The crystals were removed by vacuum filtration to afford the title compound.

1. customdid not exceed −40° C
2. additionOn completion of the addition
3. customthe cooling bath was removed
4. additionthe mixture was diluted with ether (70 mL)
5. additionpoured into 1 N sodium bisulfate solution
6. customThe phases were separated
7. washthe upper layer was washed successively with water and brine
8. dry with materialThe organic phase was dried (Na2SO4)
9. customthe solvent evaporated to half volume, at which point the product
10. customcrystallized
11. customThe crystals were removed by vacuum filtration

ORD record

ord-4aadf72e870b48d3ae2db0f0796a17c5

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07208517B1