1-chloro-3-methoxy-2-nitro-benzene synthesis
- Product Name:1-chloro-3-methoxy-2-nitro-benzene
- CAS Number:5472-99-1
- Molecular formula:C7H6ClNO3
- Molecular Weight:187.58
16554-47-5
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5472-99-1
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Yield:5472-99-1 66%
Reaction Conditions:
Stage #1: 3-methoxy-2-nitroanilinewith hydrogenchloride;sodium nitrite in water at 0; for 1 h;
Stage #2: with hydrogenchloride;copper dichloride in water at 0 - 20; for 48 h;
Steps:
88.88(A)
Example 88; 4-Chloro-2-(4-(pyridin-2-yi)but-3-ynyi)benzo[floxazoie; 88 (A) 1-Chloro-3-methoxy-2-nitrobenzene; A solution of sodium nitrite (180 mg, 2.60 mmol) in water (0.5 mL) was added dropwise to a solution of 3-methoxy-2-nitro-phenylamine (400 mg, 2.38 mmol, Example 86 (A)) HCl (37%, 3.9 mL) at 0°C over one hour period. Then the reaction mixture was added to a cold (0°C) solution of CuCl2 (640 mg, 4.76 mmol) in HCl (6 N, 3.5 mL). The resulting green solution was stirred at room temperature for 2 days. Then, the reaction mixture was poured onto ice and neutralized carefully with a saturated solution of NaHC03. The aqueous phase was extracted with AcOEt. The resulting organic phase was washed with brine, dried over MgS04, filtered and evaporated to yield 293 mg (1.56 mmol, 66%) of 1-chloro-3-methoxy-2-nitrobenzene as a brown oil.
References:
WO2005/123703,2005,A2 Location in patent:Page/Page column 139
4920-80-3
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77-78-1
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5472-99-1
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