1-(1-Ethynylhexyloxy)-2,3-difluorobenzene → 7,8-difluoro-2-pentyl-2H-chromene

HRID 2244836Notes

Reaction equation

HRID 2244836 reaction equation
[C:1]([CH:3]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=1[F:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])#[CH:2]>C(N(CC)C1C=CC=CC=1)C.CC(OC)(C)C>[F:16][C:12]1[C:11]([F:17])=[C:10]2[C:15]([CH:2]=[CH:1][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[O:9]2)=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 592152391-(1-Ethynylhexyloxy)-2,3-difluorobenzene

Product 1

HCID 592152737,8-difluoro-2-pentyl-2H-chromene

Reagents, catalysts & solvents 2

HCID 7061N,N-DiethylanilineSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

62.0 g (0.26 mol) of 1-(1-ethynylhexyloxy)-2,3-difluorobenzene are heated at 195° C. for 2 h in 390 ml of N,N-diethylaniline. The batch is diluted with MTBE and washed a number of times with 1 N HCl. The organic phase is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2, n-pentane:1-chlorobutane=5:1), giving 7,8-difluoro-2-pentyl-2H-chromene as a brown oil.

Workup

  1. washwashed a number of times with 1 N HCl
  2. customThe organic phase is dried
  3. concentrationconcentrated to dryness
  4. customThe residue is purified by column chromatography (SiO2, n-pentane:1-chlorobutane=5:1)

Sources & evidence

ORD record
ord-92890d6f913a42d7ac51efd2a663901f
Source dataset
uspto-grants-2010_03
Patent number
US07678929B2

Reaction notes

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