Water → HCID 548672, compound

HRID 1403066Notes

Reaction equation

HRID 1403066 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-a1f45bf77a064dcfa92e14f2a35a66e6
Source dataset
uspto-grants-2014_12
Patent number
US08912191B2

Reaction notes

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