Potassium Nitrate → HCID 86727380, compound

HRID 519216Notes

Reaction equation

HRID 519216 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[N+:12]([O-])([O-:14])=[O:13].[K+]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 27249122'-Fluoro-4'-hydroxyacetophenone

Product 1

HCID 86727380HCID 86727380, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a mixture of 1-(2-fluoro-4-hydroxy-phenyl)-ethanone (Alfa, 5 g, 32.5 mmol) in concentrated sulfuric acid (50 mL) at −5° C. was added KNO3 (3.29 g, 32.6 mmol) and the reaction mixture was stirred for 3 h. The reaction mixture was poured into ice water (500 mL) carefully and the aqueous solution was extracted with EtOAc (3×150 mL). The combined organic phase was washed with brine (100 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by column chromatography on silica gel (eluting with 2-10% EtOAc in petroleum ether) to give 1-(2-fluoro-4-hydroxy-5-nitro-phenyl)-ethanone as yellow solid (4.59 g, 71%). 1H NMR (CDCl3, 400 MHz): δ 10.95 (s, 1H), 8.79 (d, J=7.2 Hz, 1H), 6.92 (d, J=11.2 Hz, 1H), 2.63 (d, J=5.2 Hz, 3H).

Workup

  1. extractionthe aqueous solution was extracted with EtOAc (3×150 mL)
  2. washThe combined organic phase was washed with brine (100 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by column chromatography on silica gel (eluting with 2-10% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-0750a5d50bd14d55815d6e16b67bb891
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

Loading…