2-Bromo-4-fluoro-6-methylbenzenamine

Step a2-Bromo-4-fluoro-6-methylanilineA solution of N-bromosuccinimide (18.7 g, 0.105 mol) in 70 mL of N, N-dimethylformamide was added dropwise to a solution of 4-fluoro-2-methylaniline in 70 mL of N, N-dimethylformamide at 20 A solution of N-bromosuccinimide (18.7 g, 0.105 mol) in 70 mL of N, N-dimethylformamide was added dropwise to a solution of 4-fluoro-2-methyl-phenylamine (XI) (12.5 g, 0.1 mol) in 70 mL of the same solvent at 20°C. The reaction mixture was stirred overnight. The dark solution was poured into a mixture of water (1000 mL), brine (50 mL) andethyl acetate (300 mL). The mixture was transferred into a separatory funnel, shaken and separated. The aqueous phase was extracted with ethyl acetate (4 x 150 mL). The combined organic layers were washed with water (5 x 100 mL), brine (2 x 100 mL), dried over Na2SO4, filtered and concentrated. The product was purified by flash chromatography (eluent ethyl acetate : n-hexane = 1: 8). The pure fractions were combined and evaporated to give 14.9 g of product. The impure fractions were combined, concentrated, re-dissolved in diethyl ether (30 mL) andextracted with 5 percent hydrochloric acid (5 x 10 mL). The acidic phase was basified with aqueous potassium hydroxide and extracted with diethyl ether to provide further 0.8 g of the title compound. Total yield was 15.7 g (77percent).1H NMR (400.5 MHz, DMSO-d6) ppm 2.16 (s, 3H), 4.83 (br. s, 2H), 6.91 (dd, JH-F 9.3 Hz, JH-H 2.9 Hz, 1H), 7.16(dd, JH-F = 8.3 Hz, JH-H = 2.9 Hz, 1 H).

Molecular Weight:204.04
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:202.97459
Monoisotopic Mass:202.97459
Topological Polar Surface Area:26
Heavy Atom Count:10
Complexity:120
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes