Potassium Carbonate → 1-Chloro-4-(4-ethynylphenoxy)-2-(trifluoromethyl)benzene

HRID 920323Notes

Reaction equation

HRID 920323 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2C=O)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18].COP([C:27](=[N+]=[N-])[C:28](=O)C)(=O)OC.C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[CH:11][C:12]([C:27]#[CH:28])=[CH:13][CH:14]=2)=[CH:4][C:3]=1[C:17]([F:18])([F:19])[F:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 86676377(4-Chloro-3-(trifluoromethyl)phenoxy)benzaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 866763761-Chloro-4-(4-ethynylphenoxy)-2-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (4-chloro-3-(trifluoromethyl)phenoxy)benzaldehyde (1.82 g, 6.0 mmol) and dimethyl(1-diazo-2-oxopropyl)phosphonate (2.3 g, 12.1 mmol) in methanol (30 mL), was added potassium carbonate (4.18 g, 30.3 mmol), and stirred for 1 h at rt. The reaction mixture was concentrated and the residue was purified by FC (PE/EtOAc 20:1) to afford the title compound as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by FC (PE/EtOAc 20:1)

Sources & evidence

ORD record
ord-4a6f68f41378454a9ae29810213863a2
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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