Einecs 211-027-4 → 1-(2-Fluoro-3-hydroxy-6-nitrophenyl)propan-2-one

HRID 1163051Notes

Reaction equation

HRID 1163051 reaction equation
C([O:8][C:9]1[C:10]([F:22])=[C:11]([CH2:18][C:19](=[O:21])[CH3:20])[C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=1)C1C=CC=CC=1.[Cl-].[NH+]1C=CC=CC=1>Cl.C(OCC)(=O)C>[F:22][C:10]1[C:9]([OH:8])=[CH:14][CH:13]=[C:12]([N+:15]([O-:17])=[O:16])[C:11]=1[CH2:18][C:19](=[O:21])[CH3:20]

Participants

5

Reactant 2

HCID 69401Einecs 211-027-4HCID 112896631-(3-(Benzyloxy)-2-fluoro-6-nitrophenyl)propan-2-one

Product 1

HCID 223379951-(2-Fluoro-3-hydroxy-6-nitrophenyl)propan-2-oneYield 81.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

Method R-2: A mixture of 1-(3-benzyloxy-2-fluoro-6-nitrophenyl)-propan-2-one (65.0 g, 0.214 mol) and pyridinium chloride (60.74 g, 0.526 mol) was stirred at 180° C. for 1 hr. The reaction mixture was cooled to room temperature, diluted with 3N HCl (100 mL) and ethyl acetate (500 mL) and filtered. The aqueous layer was extracted with ethyl acetate (2×) and the combined organic layers were washed with brine, dried (MgSO4),s filtered through a pad of silica gel and concentrated in vacuo. The residue was decolorized with charcoal in methanol, filtered and concentrated in vacuo to afford 1-(2-fluoro-3-hydroxy-6-nitrophenyl)-propan-2-one (37 g, 81%) as a brown solid. LC/MS; (M+H)+=213.2

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×)
  4. washthe combined organic layers were washed with brine, dried (MgSO4),s
  5. filtrationfiltered through a pad of silica gel
  6. concentrationconcentrated in vacuo
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-52f01630e5334fce86a869743bf1846c
Source dataset
uspto-grants-2010_10
Patent number
US07820814B2

Reaction notes

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