3,4-Dichlorophenol → HCID 66667642, compound

HRID 508445Notes

Reaction equation

HRID 508445 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[Br:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:19]Br)=[C:15]([CH:18]=1)[C:16]#[N:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CCOC(C)=O>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:19][O:9][C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)=[C:15]([CH:18]=1)[C:16]#[N:17]

Participants

6

Reactant 3

HCID 72583,4-DichlorophenolHCID 11430Potassium CarbonateHCID 442031405-Bromo-2-(bromomethyl)benzonitrile

Product 1

HCID 66667642HCID 66667642, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 3,4-dichlorophenol (267.1 mg, 1.639 mmol), 5-bromo-2-(bromomethyl)benzonitrile (447.3 mg, 1.627 mmol), and potassium carbonate (674.1 mg, 4.877 mmol) in acetone (20 mL) was heated to 75° C. under nitrogen for 18 hours. The reaction mixture was cooled to room temperature, diluted with EtOAc (20 mL) and filtered through arbocel. The arbocel was then washed with EtOAc (2×20 mL), and the combined organics were washed with brine (3×20 mL), dried over sodium sulphate, filtered and concentrated in vacuo to afford the title compound as a white solid (549.9 mg, 95%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through arbocel
  3. washThe arbocel was then washed with EtOAc (2×20 mL)
  4. washthe combined organics were washed with brine (3×20 mL)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e55cb8133f7141579cdde3c391779dd8
Source dataset
uspto-grants-2015_08
Patent number
US09096500B2

Reaction notes

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