3,4-Dichlorophenol → HCID 58046350, compound

HRID 2359294Notes

Reaction equation

HRID 2359294 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].F[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=1[O:19][CH3:20].C(=O)([O-])[O-:22].[Cs+].[Cs+].[OH-].[Na+]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[O:9][C:11]1[CH:18]=[CH:17][C:14]([C:15]([NH2:16])=[O:22])=[CH:13][C:12]=1[O:19][CH3:20]

Participants

6

Reactant 4

HCID 72583,4-DichlorophenolHCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 27373654-Fluoro-3-methoxybenzonitrile

Product 1

HCID 58046350HCID 58046350, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3,4-dichlorophenol (539 mg, 3.31 mmol), 4-fluoro-3-methoxybenzonitrile (500 mg, 3.31 mmol) and cesium carbonate (2.16 g, 6.62 mmol) in DMSO (5 mL) was heated to 120° C. for 18 hours. The reaction was cooled before the addition of 1N NaOH. The reaction was extracted with ethyl acetate and the organic layer separated and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 0-20% EtOAc in heptane to furnish the title compound as a white solid, 142 mg, 14%.

Workup

  1. extractionThe reaction was extracted with ethyl acetate
  2. customthe organic layer separated
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified
  5. washeluting with 0-20% EtOAc in heptane

Sources & evidence

ORD record
ord-786a4683cdd34a9583ec8bcfc01fb61f
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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