3-CHLORO-2-NITROPHENOL

Light yellow crystalline

Step i :2-Chloro-6-fluoronitrobenzene 10a (6.62 g, 37.7 mmol) and LiOH monohydrate (6.33 g, 151 mmol) are dissolved in THF (45 mL) and water (65 mL) and an aqueous solution of H2-Chloro-6-fluoronitrobenzene 10a (6.62 g, 37.7 mmol) and LiOH monohydrate (6.33 g, 2-Chloro-6-fluoronitrobenzene 10a (6.62 g, 37.7 mmol) and LiOH monohydrate (6.33 g, 151 mmol) are dissolved in THF (45 mL) and water (65 mL) and an aqueous solution of H2-Chloro-6-fluoronitrobenzene 10a (6.62 g, 37.7 mmol) and LiOH monohydrate (6.33 g, 151 mmol) are dissolved in THF (45 mL) and water (65 mL) and an aqueous solution of HTo a solution of 1-chloro-3-fluoro-2-nitrobenzene (lOg, 57.lmmol) in THF (65mL) and H20 (lOOmL) mixture was added LiOH.H20 (9.6g, 22.8mmol) at rt. The reaction mixture was sealed and stirred at 60 00 for 72h. The reaction mixture was cooled to rt and poured in aq saturated sodium thiosulphate (lOOmL) solution. The resulted mixture was acidified with iN HCI and extracted with EtOAC (3xlOOmL). The organic layer was washed with brine (lOOmL), dried (Na2504), filtered and concentrated under reduced pressure. The residue was purified by column chromatography using silica gel (100-200 mesh), eluting with 10percent EtOAc in hexane to afford 3-chloro-2-nitrophenolas a yellow liquid. Yield: 6.0 g (51percent); 1H NMR (400 MHz, DMSO-d6): 11.50 (bs, 1H), 7.36-7.43 (m, 1H), 7.04-7.12 (m, 2H); MS (ESI-) for CHNOS m/z 172.07[M-H].Under ice cooling, ammonium nickel(II) sulfate hexahydrate (5.9 g, 15 mmol) was added to a solution of 3-chlorophenol (3.9 g, 30 mmol) in dichloromethane (45 mL), nitric acid (specific gravity 1.42, 2.5 mL) was slowly added dropwise to the mixture, and the resulting mixture was warmed to room temperature, and stirred for 3 hours.

Molecular Weight:173.55
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:172.9879707
Monoisotopic Mass:172.9879707
Topological Polar Surface Area:66
Heavy Atom Count:11
Complexity:158
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes