Nitric Acid → 5'-Fluoro-2'-hydroxy-3'-nitroacetophenone

HRID 2167729Notes

Reaction equation

HRID 2167729 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:7]=[CH:8][C:9]([OH:15])=[C:10]([C:12](=[O:14])[CH3:13])[CH:11]=1>C(O)(=O)C>[F:5][C:6]1[CH:7]=[C:8]([N+:1]([O-:4])=[O:2])[C:9]([OH:15])=[C:10]([C:12](=[O:14])[CH3:13])[CH:11]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 959922-Acetyl-4-fluorophenol

Product 1

HCID 27589845'-Fluoro-2'-hydroxy-3'-nitroacetophenone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Cone. HNO3 (22.49 g, 357 mmol) was added to a solution 1-(5-fluoro-2-hydroxyphenyl)ethanone (50 g, 325 mmol) in acetic acid (300 mL) at 0° C. and stirring was continued at 20° C. for 3 h. The reaction mixture was quenched with ice cold water. The separated solid was filtered and washed with cold water and dried to afford 1-(5-fluoro-2-hydroxy-3-nitrophenyl)ethanone (Int-49) as pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.6 (1H, s), 8.3-8.2 (1H, dd), 8.2-8.1 (1H, dd), 2.7 (3H, s).

Workup

  1. customThe reaction mixture was quenched with ice cold water
  2. filtrationThe separated solid was filtered
  3. washwashed with cold water
  4. customdried

Sources & evidence

ORD record
ord-ac0bc9ce1c4b4850a017d378aa5c0870
Source dataset
uspto-grants-2015_06
Patent number
US09045478B2

Reaction notes

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