2-Chloro-6-nitrophenol

yellow crystalline powder

To a of solution of 2-chlorophenol (0.155 mol, 15.8 mL) in glacial acetic acid (42 mL) chilled to 5 °C, nitric acid (0.163 mol, 6.8 mL) was added dropwise over a period of 45 minutes with constant magnetic stirring. The reaction was maintained at 5 °C for thirty minutes then poured over ice (~250 mL). The black solid which forms during the reaction is removed by filtration. The resulting dark brown liquid was steam distilled providing a yellow soild which was recrystalized from water to give the title compound in an 18percent yield.General procedure: To a solution of phenol (1 mmol) in acetone (5 mL) wasadded silica supported Al(NO3)3·9H2O (1 mmol) and theresulting mixture stirred at room temperature. After completionof the reaction, as indicated by TLC, the reaction masswas filtered and the residue (silica) was washed with ethylacetate (2 5 mL). The filtrate and the washing were collectivelyconcentrated under reduced pressure, and the crudecompound was purified by column chromatography oversilica gel (100-200 mesh) to afford the pure ortho-nitro phenol(95percent) and para- nitro phenol (3percent).General procedure: A suspension of 2-methylphenol(18.5 mmol, 1.0 eq) and Cu(NOGeneral procedure: To a mixture of anilines or phenols (0.7 mmol) the brominatingagent (1) (0.72 g, 0.7 mmol) in dichloromethane(30 ml)-methanol (15 ml) was added. The reactionmixture was stirred at room temperature until decolorizationof the orange solution took place. The progress of thereaction was monitored by TLC (eluent: n-hexane/ethylacetate, 7:3). After completion of the reaction, the solventwas evaporated and diethyl ether (10 ml) was added to theresidue. The supernatant was decanted and the insolubleresidue was washed by ether (3 × 10 ml). The combinedether extracts were dried on magnesium sulfate and also evaporated under vacuum to afford monobromo anilines ormonobromo phenols which was purified by flash columnchromatography over silica gel (n-hexane/ethyl acetate, 7:3).

Molecular Weight:173.55
XLogP3:2.6
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