Nitric Acid → HCID 71008792, compound

HRID 1626078Notes

Reaction equation

HRID 1626078 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:8]=1[C:15](=[O:17])[CH3:16].[N+:18]([O-])([OH:20])=[O:19]>O>[F:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([N+:18]([O-:20])=[O:19])=[CH:9][C:8]=1[C:15](=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 5928212'-Fluoro-4'-methoxyacetophenone

Product 1

HCID 71008792HCID 71008792, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-15 °C

Procedure

Sulfuric acid (157 g, 85.2 ml, 1.6 mol) was cooled to −20° C. and 1-(2-fluoro-4-methoxyphenyl)ethanone (25 g, 149 mmol) was added portionwise in a manner that the temperature was kept below −15° C. Thereafter, a solution of sulfuric acid (64.4 g, 35 ml, 657 mmol) and fumic nitric acid (18.7 g, 12.4 ml, 297 mmol) was added dropwise within 20 minutes keeping the temperature below −15° C. After completion of the addition the viscous reaction mixture was stirred for additional 20 minutes at −15° C. For the workup, the reaction mixture was poured into a mixture of ice and water (400 ml) and stirring was continued for 10 minutes. The off-white suspension was filtrated and washed several times with water. The light yellow solid was dried at 45° C. before it was crystallized from a mixture of ethyl acetate and heptane (200 ml-600 ml, addition of charcoal). The 1-(2-fluoro-4-methoxy-5-nitro-phenyl)-ethanone (26.1 g, 82% yield) was obtained as pale yellow crystals. MS (ISP): m/z=214.2 [M+H]+. In addition, the regioisomer 1-(2-fluoro-4-methoxy-3-nitro-phenyl)-ethanone (0.6 g, 2% yield) was obtained as a white solid.

Workup

  1. customwas kept below −15° C
  2. customthe temperature below −15° C
  3. additionAfter completion of the addition the viscous reaction mixture
  4. stirringstirring
  5. waitwas continued for 10 minutes
  6. filtrationThe off-white suspension was filtrated
  7. washwashed several times with water
  8. customThe light yellow solid was dried at 45° C. before it
  9. customwas crystallized from a mixture of ethyl acetate and heptane (200 ml-600 ml, addition of charcoal)

Sources & evidence

ORD record
ord-88dea4d7a16a42bb9e8c4a839b348a63
Source dataset
uspto-grants-2014_07
Patent number
US08785436B2

Reaction notes

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