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

To a mixture of 3-nitrophenol (5.0 g, 35.94 mmol), K2CO3 (7.45 g, 53.9 mmol), in 2-butanone at 85° C. 1-bromo-2-chloroethane (1.723 mL, 71.88 mmol) was added and stirred for 24 h. The mixture was cooled to rt and reduced in vacuo, then diluted with EtOAc (200 mL) and water (200 mL) and separated. The aqueous layer was extracted twice with EtOAc (200 mL) and the combined organic layers were dried over MgSO4 and reduced in vacuo onto silica. Purified via column chromatography using gradient of EtOAc/Hexanes to afford a yellow oil that solidified upon standing to afford 4.22 g (58% yield) of desired product as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 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. customat 85° C
2. customseparated
3. extractionThe aqueous layer was extracted twice with EtOAc (200 mL)
4. dry with materialthe combined organic layers were dried over MgSO4
5. customPurified via column chromatography
6. customto afford a yellow oil

ORD record

ord-00bbdbb609644558964ac929e2719a81

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07812022B2