4-Bromo-3-chloro-6-methoxyaniline

Intermediate 6: 4-Bromo-5-chloro-2-methoxyaniline A mixture of 5-chloro-2-methoxyaniline (Intermediate 5, 76.7 g, 0.487 mol) in acetonitrile (500 mL) at 0 °C was treated with N-bromosuccinimide (86.7g, 0.487 mol) added in portions over 2 h. After the addition, the solvent was removed and the residue purified by column chromatography (silica: 200 - 300 mesh, 200 g) eluting with petroleum ether/ ethyl acetate from 20:1 to 4: 1 ) to give 4-bromo-5-chloro-2- methoxyaniline as a light-yellow solid (40.2 g, 35percent). LCMS(A): Rt 1.63 min, MHTo 5-chloro-2-methoxyaniline (132 g, 0.84 mol) in acetonitrile (1000 mL), Nbromosuccinimide (150 g, 0.84 mol) was added in portions at 0 °C over 1 h. After addition, the mixture was stirred at ambient temperature for 16 h. This reaction was repeated 3 times and the 4 reactions combined. The mixture was poured into ice/water (4 kg x 2) and stirred for 1 h. The mixture was basified with solid sodium bicarbonate to between pH7 and 8. The aqueous layer was extracted with ethyl acetate (2L x 3), the combined organic layer dried over sodium sulphate, filtered and the solvent was evaporated under vacuum. The residuewas purified by column chromatography (silica, 200-300 mesh, 4 Kg, petroleum ether / ethyl acetate 50:1 to remove dibromo by-product, then petroleum ether / ethyl acetate 10:1) to give 4-bromo-5-chloro-2-methoxyaniline as a light-brown solid (380 g).A 500-mL round-bottom flask was charged with (E)-/er/-butyl 3-(3-methoxy-3-oxoprop-l-en-l-yl)-4-(((trifluoromethyl)sulfonyl)oxy)-5, 6-dihydropyridine-l(2H)-carboxylate (Preparation 3a, (10.8 g, 26.0 mmol), xantphos (1.88 g, 3.25 mmol), cesium carbonate (25.4 g, 78.0 mmol),

Molecular Weight:236.49
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:234.93995
Monoisotopic Mass:234.93995
Topological Polar Surface Area:35.2
Heavy Atom Count:11
Complexity:136
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes