Aniline → 2-Bromo-N-phenylacetamide

A solution of aniline (0.016 mol) in 40 mL of dichloromethane is cooled on ice, and 1.0 equivalent of bromoacetyl bromide in 3 mL of dichloromethane is added dropwise, followed by 0.019 mol of triethylamine (TEA). The solution turns dark and a precipate forms, as the reaction mixture is warmed to RT over 3 h. The mixture is concentrated and taken up in ethyl acetate (EtOAc) and washed three times with water. The organic phase is dried over anhydrous sodium sulphate (Na2SO4), filtered and concentrated. The residue is purified by crystallization from EtOAc to afford 2-bromo-N-phenylacetamide: m.p. 131-135° C.; 1H-NMR (CDCl3) δ 4.01 (s, 2H), 7.18 (m, 1H), 7.36 (m, 2H), 7.54 (2H), 8.09 (s, 1H).

1. additionis added dropwise
2. concentrationThe mixture is concentrated
3. washwashed three times with water
4. dry with materialThe organic phase is dried over anhydrous sodium sulphate (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue is purified by crystallization from EtOAc

ORD record

ord-3708509d9862409da9476ded7f147adf

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07767685B2