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

HRID 445824Notes

Reaction equation

HRID 445824 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-8cffebecfee74664a4c856a4107d29e8
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

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