2-FLUORO-5-NITROPHENYLACETIC ACID

Light yellow crystalline

To a solution of o-fluoro benzoic acid (30.0 g, 0.19mol) in cone, sulfuric acid (50 mL) and water (10 mL) was added dropwise a solution of fuming nitric acid (10 mL) in water (10 mL) at 0 2-Fluoro-5-nitrophenyl)acetic acid (commercially available, 3.0 g, 15 mmol), dimethyl amine (10% in THF, 10.1 g, 22.6 mmol) and HATU (11.45 g, 30.1 mmol) in DMF (30 ml) was added to a RBF previously equipped with a magnetic stirrer and nitrogen balloon and the mixture was cooled to O C. After 30 minutes, A/./V-Diisopropylethylamine (5.20 ml) was added drop wise and the reaction mixture was stirred at room temperature for 3 h. The reaction mixture was quenched with water (150 ml). The product was extracted with ethyl acetate (3 x 100 ml) and the combined organic layer was washed with brine (100 ml). The organic layer was dried over sodium sulphate and the solvent evaporated under reduced pressure. The crude product was purified by combi flash chromatography using 2% Methanol in DCM as an eluent to obtain 3.6 g of the title compound. 1 H NMR (400 MHz, DMSO-cfe) d 8.27 - 8.20 (m, 2H), 7.48 (t, J = 9.0 Hz, 1 H), 3.92 (s, 2H), 3.10 (s, 3H), 2.87 (s, 3H); MS (ES+) m/z 227 [M+H]+

Molecular Weight:199.14
XLogP3:1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:199.02808583
Monoisotopic Mass:199.02808583
Topological Polar Surface Area:83.1
Heavy Atom Count:14
Complexity:240
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes