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Potassium Carbonate → 5-[3-(Benzyloxy)-2-fluoro-4-nitrophenoxy]-2-(methylsulfonyl)pyridine

HRID 1188954
Notes
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Reaction equation

HRID 1188954 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([F:15])=[C:13](F)[CH:12]=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][S:21]([C:24]1[N:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)(=[O:23])=[O:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:14]([F:15])=[C:13]([CH:12]=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18])[O:30][C:27]1[CH:26]=[CH:25][C:24]([S:21]([CH3:20])(=[O:23])=[O:22])=[N:29][CH:28]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 178588811-Benzyloxy-2,3-difluoro-6-nitrobenzeneHCID 231451966-(Methylsulfonyl)pyridin-3-ol

Product 1

HCID 582371085-[3-(Benzyloxy)-2-fluoro-4-nitrophenoxy]-2-(methylsulfonyl)pyridineYield 69.6%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(benzyloxy)-3,4-difluoro-1-nitrobenzene (7.65 g), 6-(methylsulfonyl)pyridin-3-ol (5.0 g) and potassium carbonate (4.4 g) in N,N-dimethylformamide (40 mL) was stirred at 90° C. for 5 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed with successively water and brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:hexane=25:75 to 40:60, volume ratio) to give light yellow crystals, which were washed with ethyl acetate-hexane to give the title compound (8.4 g, 69%) as pale yellow crystals.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with successively water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (ethyl acetate:hexane=25:75 to 40:60, volume ratio)
  8. customto give light yellow crystals, which
  9. washwere washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-168cd5ef4299453f933c46a20bd7ccc2
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08673942B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes