4'-Fluoroacetophenone → HCID 57585848, compound

HRID 547635Notes

Reaction equation

HRID 547635 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O>[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=2)=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 98284'-FluoroacetophenoneHCID 10796Cesium carbonateHCID 37588824-Amino-3-Nitrophenol

Product 1

HCID 57585848HCID 57585848, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(4-Fluorophenyl)ethanone (1.79 g, 12.9 mmol), 4-amino-3-nitrophenol (2 g, 12.9 mmol) and Cs2CO3 (4.65 g, 14.3 mmol) were stirred in 50 mL of dimethylformamide at 80 degrees Centigrade for 24 hours. The solids were filtered away. The filtrate was diluted with ethyl acetate and washed with water and brine three times each. The aqueous layers were back extracted twice with ethyl acetate. The organic layers were combined, dried over MgSO4 and concentrated onto basic alumina. The crude product was purified by silica gel column chromatography (hexanes to ethyl acetate gradient) to give 1-{4-[(4-amino-3-nitrophenyl)oxy]phenyl}ethanone. (M+1) 272.9, 2.42 min (LC/MS method B)

Workup

  1. filtrationThe solids were filtered away
  2. additionThe filtrate was diluted with ethyl acetate
  3. washwashed with water and brine three times each
  4. extractionThe aqueous layers were back extracted twice with ethyl acetate
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated onto basic alumina
  7. customThe crude product was purified by silica gel column chromatography (hexanes to ethyl acetate gradient)

Sources & evidence

ORD record
ord-d63fe6cb4fdb4eb3acda6ce6e226b5dc
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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