Bromine → 2-Methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-6-thiocyanato-phenylamine

To a solution of 2-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenylamine (5.0 g, 18.20 mmol) (prepared according to EP 1,006,102) in acetic acid (30 ml) was added a solution of potassium thiocyanate (7.25 g, 74.62 mmol) in acetic acid (20 ml). The solution was cooled to 5° C. before the addition of bromine (3.2 g, 1.03 ml) in acetic acid (10 ml). The reaction mixture was allowed to warm to ambient temperature and was stirred at ambient temperature for 3 hours. The reaction mixture was quenched by pouring into water. The mixture was extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed successively with aqueous sodium hydroxide (10 g/l) (100 ml), water (100 ml) and brine (100 ml), dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/cyclohexane 1:3) to give 2-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-6-thiocyanato-phenylamine (3.7 g, 61.2% yield). 1H-NMR (CDCl3, 400 MHz): 7.68 (s, 1H), 7.33 (s, 1H), 5.73 (s, 2H), 2.59 (s, 6H) ppm.

1. customThe reaction mixture was quenched
2. additionby pouring into water
3. extractionThe mixture was extracted with ethyl acetate (3×100 ml)
4. washThe combined organic extracts were washed successively with aqueous sodium hydroxide (10 g/l) (100 ml), water (100 ml) and brine (100 ml)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated
7. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/cyclohexane 1:3)

ORD-Eintrag

ord-37c92d03563347eabfd01fe1fd482665

Quelldatensatz

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08389767B2