Tetrahydrofuran → 4,5-Dichloro-2-methylaniline

Temperature

100 °C

To a partial suspension of 1,2-dichloro-4-methyl-5-nitrobenzene (2.0 g, 9.71 mmol) in MeOH (25 ml), water (25 ml), and THF (10 ml) was added NH4Cl (5.19 g, 97.1 mmol) followed by iron powder (2.71 g, 48.5 mmol). The heterogeneous reaction mixture was heated at 100° C. for 3 h then cooled to room temperature and filtered over a Buchner funnel, rinsing with MeOH. The filtrate was diluted with water and saturated aqueous NaHCO3 then extracted with CH2Cl2 (3×). The combined organics were dried over MgSO4 and concentrated to afford 1.69 g (99%) of 4,5-dichloro-2-methylaniline as a white solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 7.10 (s, 1H), 6.75 (s, 1H), 3.74 (br. s., 2H), 2.12 (s, 3H).

1. temperaturethen cooled to room temperature
2. filtrationfiltered over a Buchner funnel
3. washrinsing with MeOH
4. additionThe filtrate was diluted with water and saturated aqueous NaHCO3
5. extractionthen extracted with CH2Cl2 (3×)
6. dry with materialThe combined organics were dried over MgSO4
7. concentrationconcentrated

ORD record

ord-ee13f308c706464ab23b5a7a4732734e

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658646B2