Water → HCID 548672, compound

HRID 217875Notes

Reaction equation

HRID 217875 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[OH:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.CCOC(C)=O>[N+:12]([C:3]1[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=1[O:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 962WaterHCID 79713-HydroxypyridineHCID 10796Cesium carbonateHCID 677784-Fluoro-3-nitrobenzotrifluoride

Product 1

HCID 548672HCID 548672, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A brown solution of 1-fluoro-2-nitro-4-(trifluoromethyl)benzene (2.01 g, 9.61 mmol) and 3-hydroxypyridine (0.923 g, 9.71 mmol) in dry DMF (15 ml) under Ar was treated with cesium carbonate (3.28 g, 10.07 mmol) at once and the brown mixture was stirred at RT for 2 h. H2O (50 mL) and EtOAc (50 mL) were added and the organic layer was isolated. The water layer was extracted with EtOAc (2×30 mL). The combined organic layer was washed with H2O (3×40 mL), brine (40 mL), dried (MgSO4), filtered and concentrated to dryness to give a light yellow solid. Yield: 2.62 g (96%).

Workup

  1. customthe organic layer was isolated
  2. extractionThe water layer was extracted with EtOAc (2×30 mL)
  3. washThe combined organic layer was washed with H2O (3×40 mL), brine (40 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customto give a light yellow solid

Sources & evidence

ORD record
ord-b608616733e742b0b2844e428bdff4f1
Source dataset
uspto-grants-2012_06
Patent number
US08198279B2

Reaction notes

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