4-Fluoro-3-nitrobenzotrifluoride → HCID 26189352, compound

HRID 1042679Notes

Reaction equation

HRID 1042679 reaction equation
C([O-])(O)=O.[Na+].F[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=1[N+:17]([O-])=O.[CH3:20][N:21]([CH3:26])[CH2:22][CH2:23][CH2:24][OH:25].CC(C)([O-])C.[K+]>C1COCC1>[CH3:20][N:21]([CH3:26])[CH2:22][CH2:23][CH2:24][O:25][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=1[NH2:17]

Participants

6

Reactant 4

HCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 766463-(Dimethylamino)-1-propanolHCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 26189352HCID 26189352, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of NaHCO3 (3.9 g, 48 mmol), 1-fluoro-2-nitro-4-trifluoromethylbenzene (4.0 g, 19 mmol), and 3-dimethylamino-1-propanol (2.5 ml, 21 mmol) in 38 mL dry THF was heated with a reflux condenser under nitrogen for 12 h. The mixture was filtered through a fritted funnel into a flask. The solution was cooled to 0° C. and was treated with potassium tert-butoxide (2.4 g, 21 mmol) resulting in an orange solution. The solution was warmed to ambient temperature and was allowed to stir for 1 h. The solvent was removed in vacuo, and the resulting brown oil was partitioned between saturated aqueous NaHCO3 and methylene chloride. The aqueous layer was extracted three times with methylene chloride. The combined organic layers were dried with Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography (MC/MeOH/conc. NH4OH) to provide the desired compound as an orange oil. MS (m/z): 293.1 (M+H)+. Calc'd for C12H15F3N2O3: 292.25.

Workup

  1. temperaturewas heated with a reflux condenser under nitrogen for 12 h
  2. filtrationThe mixture was filtered through a fritted funnel into a flask
  3. customresulting in an orange solution
  4. temperatureThe solution was warmed to ambient temperature
  5. customThe solvent was removed in vacuo
  6. customthe resulting brown oil was partitioned between saturated aqueous NaHCO3 and methylene chloride
  7. extractionThe aqueous layer was extracted three times with methylene chloride
  8. dry with materialThe combined organic layers were dried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel chromatography (MC/MeOH/conc. NH4OH)

Sources & evidence

ORD record
ord-8a1faaeb8e984cb8adf17692c06c35c4
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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