N,N-Diethylaniline → 4-Bromo-6,7-difluoro-2-methylbenzofuran

HRID 2244845Notes

Reaction equation

HRID 2244845 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:10][CH2:11][C:12]#C)[C:5]([F:9])=[C:6]([F:8])[CH:7]=1.[F-].[Cs+].[CH2:16](N(CC)C1C=CC=CC=1)C>CC(OC)(C)C>[Br:1][C:2]1[C:3]2[CH:16]=[C:11]([CH3:12])[O:10][C:4]=2[C:5]([F:9])=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 3

HCID 7061N,N-DiethylanilineHCID 25953Cesium fluorideHCID 592152525-Bromo-1,2-difluoro-3-prop-2-ynyloxybenzene

Product 1

HCID 592152424-Bromo-6,7-difluoro-2-methylbenzofuran

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

51.9 g (0.21 mol) of 5-bromo-1,2-difluoro-3-prop-2-ynyloxybenzene are heated at 205° C. for 4 h together with 20.7 g (0.14 mol) of caesium fluoride in 300 ml of N,N-diethylaniline. The batch is diluted with MTBE and washed a number of times with 1 N HCl. The solution is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2, n-heptane:1-chlorobutane=3:1), giving 4-bromo-6,7-difluoro-2-methylbenzofuran as a yellow solid.

Workup

  1. washwashed a number of times with 1 N HCl
  2. customThe solution is dried
  3. concentrationconcentrated to dryness
  4. customThe residue is purified by column chromatography (SiO2, n-heptane:1-chlorobutane=3:1)

Sources & evidence

ORD record
ord-734869114e0e4fcc9f1c94bcaf0cda5f
Source dataset
uspto-grants-2010_03
Patent number
US07678929B2

Reaction notes

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