Nitric Acid → HCID 24721623, compound

HRID 715083Notes

Reaction equation

HRID 715083 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1>>[F:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C:13](=[O:15])[CH3:14])=[CH:10][C:11]=1[N+:1]([O-:4])=[O:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 521187(4-Fluorophenyl)acetone

Product 1

HCID 24721623HCID 24721623, compoundYield 41.3%

Conditions

Temperature
-35 °C

Procedure

Treat a −35° C. solution of fuming nitric acid (32.3 mL, 723 mmol) with 4-fluorophenylacetone (1.756 ml, 13.14 mmol) and stir at −35° C. for 1 h. Pour the mixture onto ice, extract with DCM (2×), dry the combined organics over MgSO4, concentrate to dryness and purify via silica gel chromatography (EtOAc/Hex) to afford the title compound (1.07 g, 41%). 1H NMR (400 MHz, DMSO-d6): δ 7.97 (dd, J=7.4, 2.2 Hz, 1H), 7.58 (ddd, J=8.6, 4.6, 2.2 Hz, 1H), 7.52 (dd, J=11.3, 8.6 Hz, 1H), 3.95 (s, 2H), 2.17 (s, 3H).

Workup

  1. additionPour the mixture onto ice
  2. extractionextract with DCM (2×)
  3. dry with materialdry the combined organics over MgSO4
  4. concentrationconcentrate to dryness
  5. custompurify via silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-edc4c2de426c4874a7a81895c9bc2ffc
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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