3-BROMO-2-NITROTOLUENE

yellow crystalline low melting mass

A mixture of copper(II) bromide (3.52 g, 15.7 mmol) in 20 mL dry acetonitrile was heated to 65° C. under an N2 atmosphere. t-Butyl nitrite (2.35 mL, 2.03 g, 19.7 mmol) was added all at once. A solution of 3-methyl-2-nitroaniline (lb; 2.00 g, 13.1 mmol; J. Org Chem. 1976 41(21):3357) in 15 mL acetonitrile was added to the above solution at a rate to sufficient to maintain gentle reflux. After addition the mixture was heated at a gentle reflux for an additional 15 min. The reaction mixture was cooled to rt and partitioned between 6N HCl solution (150 mL) and ether (150 mL). The ethereal solution was separated and washed with brine, then dried over MgSO4. Evaporation of the solvent afforded 2.76 g of impure material, which was flash chromatographed on SiO2 and eluted with 10percent acetone in hexane which afforded 1.62 g (57percent) of lc as a pale yellow-green liquid.7-Bromo-2H-indazole step 1 3-Bromo-2-nitrotoluene (Scheme 1 ; IC)-A mixture of copper (II) bromide (3.52g, 15.7 mol) in 20 mL dry acetonitrile was heated to 65 °C under an N2 atmosphere. t-Butyl nitrite (2.35 mL, 2.03 g, 19.7 mmol) was added all at once. A solution of 3-methyl-2- nitroaniline (LB ; 2. 00g, 13.1 mmol; J. ORG CHEM. 1976 41 (21): 3357) in 15 mL acetonitrile was added to the above solution at a rate to sufficient to maintain gentle reflux. After addition the mixture was heated at a gentle reflux for an additional 15 M. The reaction mixture was cooled to rt and partitioned between 6N HC1 solution (150 mL) and ether (150 mL). The ethereal solution was separated and washed with brine, then dried over MGS04. Evaporation of the solvent afforded 2.76g of impure material, which was flash chromatographed on Si02 and eluted with 10percent acetone in hexane which afforded 1.62g (57percent) of lc as a pale yellow-green liquid.

Molecular Weight:216.03
XLogP3:2.8
Hydrogen Bond Acceptor Count:2
Exact Mass:214.95819
Monoisotopic Mass:214.95819
Topological Polar Surface Area:45.8
Heavy Atom Count:11
Complexity:157
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes