2-Bromo-4-trifluoromethoxyaniline

clear light yellow to orange-yellow liquid

N-Bromosuccinamide (3.62 g, 20.34 mmol) was added to a solution of commercially available 4-(trifluoromethoxy)aniline (3.00 g, 1 6.95 mmol) in acetonitrile (30 mL) at 0°C. The resulting mixture was allowed to warm to roomtemperature and stirred for 4 hours. The solvent was removed under reduced pressure to give the crude product which was purified by column chromatography eluting in 10percent ethyl acetat/hexane to afford the title compound as brown oil (3.6 gm, 83percent): 1 H NMR (400 MHz, CDCI3) ö: 4.11 (bs, 2 H), 6.73 (d, 1 H), 6.99 (dd, 1 H), 7.31 (d, 1 H). LC-Ms (m/z): [M-H] = 253.1.4-Trifluoromethoxyaniline (1.0 g, 5.6 mmol) was dissolved in glacial acetic acid (10 mL). Bromine (585 μL, 11 mmol) dissolved in glacial acetic acid (2 mL) was added with stirring during 10 minutes at room temperature. The resulting mixture was stirred at room temperature for 2 hours and then poured into water (100 mL). The solid formed (2, 5-dibromo-4-trifluoromethoxyaniline) was filtered off. The filtrate was made alkaline with solid sodium hydroxide and extracted with dichloromethane (100 mL), dried (MgSO4) and concentrated (30°C; 200 mBar) to afford 0.57 g (40percent) of 2-bromo-4-trifluoromethoxyaniline.1H NMR (DMSO-d6): δ 5.55 (2H, bs), 6.85 (1H, d), 7.10 (1H, dd), 7.37 (1H, d).According to route (C),

Molecular Weight:256.02
XLogP3:3.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:254.95066
Monoisotopic Mass:254.95066
Topological Polar Surface Area:35.2
Heavy Atom Count:13
Complexity:176
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes