Nitric Acid → HCID 15311692, compound

HRID 525931Notes

Reaction equation

HRID 525931 reaction equation
[N+:1]([O-:4])([OH:3])=[O:2].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:7]=1[O:14][CH3:15]>>[F:5][C:6]1[C:7]([O:14][CH3:15])=[C:8]([O:12][CH3:13])[CH:9]=[CH:10][C:11]=1[N+:1]([O-:4])=[O:2].[F:5][C:6]1[CH:11]=[C:10]([N+:1]([O-:3])=[O:2])[CH:9]=[C:8]([O:12][CH3:13])[C:7]=1[O:14][CH3:15]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 27589791-Fluoro-2,3-dimethoxybenzene

Product 2

HCID 15311692HCID 15311692, compoundYield 49%HCID 21999488Benzene, 2-fluoro-3,4-dimethoxy-1-nitro-Yield 28%

Procedure

To a solution of nitric acid (853 ml, 1.91E+04 mmol) stirred at 0° C. was added dropwise 1-fluoro-2,3-dimethoxybenzene (149 g, 954 mmol). The mixture was stirred at the same temperature for 15 min, and then was allowed to warm up to RT for 15 min. The orange solution was poured into ice and the resultant solid was filtered, washed with water and dried. LCMS showed that the pale yellow solid was the mixture of two products (ratio 1/1.8). The crude material was purified by reverse phase automatic C18 column chromatography (Combiflash RF, 120 g column), eluting with Acetonitrile/Water (0-90%) over 35 min to afford 2-fluoro-3,4-dimethoxy-1-nitrobenzene (53 g, 263 mmol, 28% yield) and 1-fluoro-2,3-dimethoxy-5-nitrobenzene (94 g, 467 mmol, 49% yield) as white solids. LCMS: (M+H)+: 202.1.

Workup

  1. additionThe orange solution was poured into ice
  2. filtrationthe resultant solid was filtered
  3. washwashed with water
  4. customdried
  5. additionthe mixture of two products (ratio 1/1.8)
  6. customThe crude material was purified by reverse phase automatic C18 column chromatography (Combiflash RF, 120 g column)
  7. washeluting with Acetonitrile/Water (0-90%) over 35 min

Sources & evidence

ORD record
ord-1b519746336a4aea83bc81f133ed5362
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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