Dimethylformamide → 3,5-Dichloro-4-ethoxyaniline

Temperature

0 °C

4-Amino-2,6-dichlorophenol (1) (1.00 g, 5.62 mmol) was dissolved in dry DMF (9 mL) and cooled to 0° C. Sodium hydride (142 mg, 5.90 mmol) was added to the mixture portionwise. The dark purple solution was stirred for 1 h at RT, then iodoethane (468 μL, 5.79 mmol) was added. The reaction mixture was stirred for 3 h and partitioned between EtOAc and aqueous NaOH (1 M). The organic layer was washed successively with water and brine, and then dried over MgSO4, filtered and the solvent evaporated in vacuo. The residue was purified by silica gel chromatography (5% EtOAc/isohexane) to afford 3,5-dichloro-4-ethoxyaniline (2) (460 mg, 40%): m/z 206 [M+H]+ (ES+). 1H NMR (400 MHz, CDCl3) δ: 6.60 (2H, s), 4.01 (2H, q), 3.60 (2H, s), 1.42 (3H, t).

1. stirringThe reaction mixture was stirred for 3 h
2. custompartitioned between EtOAc and aqueous NaOH (1 M)
3. washThe organic layer was washed successively with water and brine
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customthe solvent evaporated in vacuo
7. customThe residue was purified by silica gel chromatography (5% EtOAc/isohexane)

ORD record

ord-58b6bcdb0c404cfd819d84bb7c054a0d

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09447028B2