2-Bromoethanol → N-Ethyl-N-(beta-hydroxyethyl)-4-bromoaniline

Temperature

125 °C

17.3 g (86.7 mmols) of N-ethyl-4-bromoaniline, 22.7 ml (1.5-fold equivalent weight) of N,N-diisopropylethylamine and 9.64 ml (1.5-fold equivalent weight) of 2-bromoethanol were mixed, and the mixture obtained was heated at 125° C. for 2 hours in an atmosphere of argon. Next, to the reaction solution obtained, 1.5 ml (0.1-fold equivalent weight) of diisopropylethylamine and 0.64 ml (0.1-fold equivalent weight) of 2-bromoethanol were added, and the mixture obtained was heated at 125° C. for 3 hours in an atmosphere of argon. Water was added to the reaction solution obtained, which was then extracted with ethyl acetate. The organic layer obtained was dried with anhydrous magnesium sulfate and then concentrated. The residue thus obtained was purified by silica gel column chromatography developing system (chloroform) to obtain 14.7 g of N-ethyl-N-(2-hydroxyethyl)-4-bromoaniline (yield: 69.5%; a colorless oily liquid).

1. customthe mixture obtained
2. customNext, to the reaction solution obtained
3. customthe mixture obtained
4. temperaturewas heated at 125° C. for 3 hours in an atmosphere of argon
5. customobtained
6. extractionwhich was then extracted with ethyl acetate
7. customThe organic layer obtained
8. dry with materialwas dried with anhydrous magnesium sulfate
9. concentrationconcentrated
10. customThe residue thus obtained
11. customwas purified by silica gel column chromatography

ORD record

ord-007123975d5847128a691b561d3559d1

Source dataset

uspto-grants-1998_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05834575