3,4-Dichlorophenol → HCID 58046322, compound

HRID 2359284Notes

Reaction equation

HRID 2359284 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1F)[C:5]([O:7]C)=[O:6].[Cl:13][C:14]1[CH:15]=[C:16]([OH:21])[CH:17]=[CH:18][C:19]=1[Cl:20].C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[Na+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:21][C:16]1[CH:17]=[CH:18][C:19]([Cl:20])=[C:14]([Cl:13])[CH:15]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 72583,4-DichlorophenolHCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 7018022Methyl 3-bromo-4-fluorobenzoate

Product 1

HCID 58046322HCID 58046322, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

Methyl 3-bromo-4-fluorobenzoate (Preparation 122, 500 mg, 2.15 mmol), 3,4-dichlorophenol (350 mg, 2.15 mmol) and caesium carbonate (1.4 g, 4.29 mmol) were stirred in dimethylsulfoxide (10 mL). The reaction mixture was heated to 120° C. and stirred overnight under an atmosphere of nitrogen. A 1M aqueous solution of sodium hydroxide was added and the mixture extracted with ethyl acetate. The aqueous phase was acidified and extracted with ethyl acetate. The organic phase from the second extraction was concentrated in vacuo and the resulting residue was purified by silica gel column chromatography (30%-100% ethyl acetate in heptane) to afford the title compound as a white solid (244 mg, 31%).

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. extractionThe organic phase from the second extraction
  4. concentrationwas concentrated in vacuo
  5. customthe resulting residue was purified by silica gel column chromatography (30%-100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-aed94192d1b34908a7f97a1b9339f857
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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