Diazomethane → Ethyl 3-cyclopropyl-4-fluorobenzoate

HRID 401791Notes

Reaction equation

HRID 401791 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[CH:13]=[CH2:14].[N+](=[CH2:17])=[N-]>CCOCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:13]1([C:3]2[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=2[F:1])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:17][CH2:14]1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 46941363Ethyl 4-fluoro-3-vinylbenzoate

Product 1

HCID 40151794Ethyl 3-cyclopropyl-4-fluorobenzoateYield 99.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of ethyl 4-fluoro-3-vinylbenzoate (Preparation 54, 48 g, 0.25 mol, 1 eq) and palladium (II) acetate (2.5 g, 10 mmol, 0.4 eq) in ether (300 mL) was added diazomethane in ether (1.5 mol, 6.0 eq). Then the mixture was stirred at room temperature overnight. The reaction was quenched with a solution of AcOH (75 mL) in water (100 mL). The mixture was filtrated and the filtrate was added saturated solution of sodium carbonate until pH=10. The organic phase was washed with brine (200 mL) and water (200 mL), dried over sodium sulfate and concentrated in vacuo to give title compound as brown liquid (51 g, 0.248 mol, 99.1%).

Workup

  1. customThe reaction was quenched with a solution of AcOH (75 mL) in water (100 mL)
  2. filtrationThe mixture was filtrated
  3. additionthe filtrate was added saturated solution of sodium carbonate until pH=10
  4. washThe organic phase was washed with brine (200 mL) and water (200 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c15e002275ee4bff9122cb558c695a60
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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