Water → [5-(3-[1,3]Dioxan-2-yl-phenylsulfanyl)-4-fluoro-2-nitro-phenyl]-methanol

HRID 658066Notes

Reaction equation

HRID 658066 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:8]=[C:9]([SH:13])[CH:10]=[CH:11][CH:12]=1.[F:14][C:15]1[C:20](F)=[CH:19][C:18]([CH2:22][OH:23])=[C:17]([N+:24]([O-:26])=[O:25])[CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:8]=[C:9]([S:13][C:20]2[C:15]([F:14])=[CH:16][C:17]([N+:24]([O-:26])=[O:25])=[C:18]([CH2:22][OH:23])[CH:19]=2)[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 57475722(4,5-Difluoro-2-nitrophenyl)methanolHCID 578640833-[1,3]Dioxan-2-yl-benzenethiol

Product 1

HCID 86634266[5-(3-[1,3]Dioxan-2-yl-phenylsulfanyl)-4-fluoro-2-nitro-phenyl]-methanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[1,3]Dioxan-2-yl-benzenethiol (2.57 g, 14.02 mmol), prepared as described in Example 1, Step C, (4,5-difluoro-2-nitro-phenyl)-methanol (2.65 g, 14.02 mmol), and cesium carbonate (9.1 g, 28 mmol) were combined in DMF (100 mL). The resulting mixture was stirred overnight at room temperature. Water was added, and the resulting mixture was then extracted with ethyl acetate. The organic layer was dried with Na2SO4 and filtered, and the solvent was removed to yield an oil, which was purified via silica column chromatography (50% EtOAc/heptane) to yield a solid.

Workup

  1. extractionthe resulting mixture was then extracted with ethyl acetate
  2. dry with materialThe organic layer was dried with Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed
  5. customto yield an oil, which
  6. customwas purified via silica column chromatography (50% EtOAc/heptane)
  7. customto yield a solid

Sources & evidence

ORD record
ord-60138009a16e4b00b2599e700f5a3aee
Source dataset
uspto-grants-2011_12
Patent number
US08076358B2

Reaction notes

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