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89642-17-1

Benzene, 2-bromo-1-chloro-3-methyl-5-nitro- synthesis

2synthesis methods
-

Yield:89642-17-1 96.7%

Reaction Conditions:

with tert.-butylnitrite;copper(II) bromide in acetonitrile at 20; for 0.0833333 h;Cooling with ice;

Steps:

17.1 Step 1: 2-bromo-1-chloro-3-methyl-5-nitrobenzene

2-chloro-6-methyl-4-nitroaniline (500 mg, 2.68 mmol), copper bromide (718 mg, 3.22 mmol), and acetonitrile (8 mL) were added to a 25 mL three-necked bottle and stirred for 5 min under ice bath. Tert-butyl nitrite (470 mg, 4.02 mmol) was dissolved in acetonitrile (2 mL), and then added dropwise to the three-necked bottle, and the mixture was allowed to warm to room temperature, reacting overnight. H2O (20 mL) was added, and the mixture was extracted with ethyl acetate (20 mL33). The organic layers were combined, and washed with saturated sodium chloride (20 mL), and the solvent was dried with rotation under vacuum, to give the product of 2-bromo-1-chloro-3-methyl-5-nitrobenzene (yellow solid, 650 mg), with a yield of 96.7%. 1H NMR (400 MHz, CDCl3) δ 8.17 (s, 1H), 8.01 (s, 1H), 2.57 (s, 3H).

References:

EP3476829,2019,A1 Location in patent:Paragraph 0116