1-Bromo-2-Chloroethane → 1-(2-chloroethoxy)-3-nitrobenzene

To a mixture of 3-nitrophenol (5.0 g, 36 mmol) and K2CO3 (7.45 g, 54 mmol), in 2-butanone at 85° C. was added 1-bromo-2-chloroethane (1.7 mL, 71.9 mmol) and the reaction stirred for 24 h. The mixture was cooled to rt and reduced in vacuo. The crude was diluted with EtOAc (200 mL) and water (200 mL) and separated. The aqueous layer was extracted twice with EtOAc (200 mL), the organics were pooled, dried over MgSO4 and reduced in vacuo onto silica gel. Purification was achieved via column chromatography using a gradient of EtOAc/Hexanes to afford a yellow oil that solidified upon standing to afford 4.22 g (58% yield) of titled product as an off-white solid. 1H NMR (400 MHz, DMSO-D6) δ ppm 7.8 (m, 1H), 7.7 (t, J=2.4 Hz, 1H), 7.6 (t, J=8.2 Hz, 1H) 7.4 (dd, J=8.2, 2.6 Hz, 1H), 4.4 (m, 2H), 4.0 (m, 2H).

1. customseparated
2. extractionThe aqueous layer was extracted twice with EtOAc (200 mL)
3. dry with materialdried over MgSO4
4. customPurification
5. customto afford a yellow oil

ORD record

ord-bb9b5332ebbe4046b919c81eeaaaf7fe

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07807673B2