Cesium carbonate → HCID 66885609, compound

HRID 1188898Notes

Reaction equation

HRID 1188898 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([OH:14])[CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH3:3].C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:22]1[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][N:23]=1>CN(C)C=O>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[O:14][C:22]1[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][N:23]=1)[CH3:1]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 98994832-Bromo-5-(methylsulfonyl)pyridineHCID 58237059HCID 58237059, compound

Product 1

HCID 66885609HCID 66885609, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(1-methylethoxy)-4-nitrophenol (27.3 g), cesium carbonate (90.4 g), 2-bromo-5-(methylsulfonyl)pyridine (32.7 g) and N,N-dimethylformamide (250 mL) was stirred at 100° C. for 4 h. The mixture was concentrated under reduced pressure and water was added to the residue. The resulting brown suspension was filtered to collect a brown solid. The solid was washed with ethanol-hexane to give the title compound (38.82 g, 79%) as a brownish-yellow solid. MS 353 (MH+).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure and water
  2. additionwas added to the residue
  3. filtrationThe resulting brown suspension was filtered
  4. customto collect a brown solid
  5. washThe solid was washed with ethanol-hexane

Sources & evidence

ORD record
ord-1d97f83c47114cb0a5a964c5cf0b7d64
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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