Potassium Carbonate → 4-ethynyl-2-fluoro-1-methoxybenzene

HRID 2069627Notes

Reaction equation

HRID 2069627 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=O.[C:12](=O)([O-])[O-].[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CO>[C:5]([C:4]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:2]([F:1])[CH:3]=1)#[CH:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 676963-Fluoro-p-anisaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 64319824-ethynyl-2-fluoro-1-methoxybenzeneYield 166.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the mixture of 3-fluoro-4-methoxybenzaldehyde (0.589 g, 3.0 mmol), potassium carbonate (1.8 g, 13.0 mmol) in methanol (65 mL) at room temperature was added slowly dimethyl 1-diazo-2-oxopropylphosphonate (1.4 g, 7.2 mmol). The resulting mixture was stirred at room temperature for 2 hours, quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The organic phase was washed with water, brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (10% EtOAc in hexanes) to provide 4-ethynyl-2-fluoro-1-methoxybenzene (622) (0.750 g, 76.9%) as a colorless oil.

Workup

  1. customquenched with saturated sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-18cfc6c0650148b69e890e3d0cc1ed38
Source dataset
uspto-grants-2012_10
Patent number
US08299117B2

Reaction notes

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