Toluene → 7,8-Difluoro-2-propylchroman

HRID 1765001Notes

Reaction equation

HRID 1765001 reaction equation
[H-].[Na+].C1COCC1.[OH:8][CH:9]([CH2:21][CH2:22][CH3:23])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[C:13]=1F.C1(C)C=CC=CC=1>CN(C=O)C>[F:18][C:15]1[C:14]([F:19])=[C:13]2[C:12]([CH2:11][CH2:10][CH:9]([CH2:21][CH2:22][CH3:23])[O:8]2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 231157091-(3-Hydroxy-1-hexyl)-2,3,4-trifluorobenzene

Product 1

HCID 115358337,8-Difluoro-2-propylchroman

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Sodium hydride (60% in oil) was suspended in DMF under nitrogen replacement. Then, the THF solution containing 1-(3-hydroxy-1-hexyl)-2,3,4-trifluorobenzene was added dropwise for 30 minutes, and stirred for 3 hours at 50° C. After toluene was added and stirred for a while, an organic layer was separated and an aqueous layer was extracted with toluene. After the extract and the organic layer were mixed together, washed using water and a saturated saline solution in that order, and dried using anhydrous sodium sulfate, the solvent was evaporated under a reduced pressure. The residue was purified by column chromatography (silica gel, hexane) to obtain 7,8-difluoro-2-propylchroman.

Workup

  1. additionwas added dropwise for 30 minutes
  2. stirringstirred for a while
  3. customan organic layer was separated
  4. extractionan aqueous layer was extracted with toluene
  5. extractionAfter the extract
  6. additionthe organic layer were mixed together
  7. washwashed
  8. customa saturated saline solution in that order, and dried
  9. customthe solvent was evaporated under a reduced pressure
  10. customThe residue was purified by column chromatography (silica gel, hexane)

Sources & evidence

ORD record
ord-1c73bbdccbbe4c2da4b9bac9e9733642
Source dataset
uspto-grants-2007_06
Patent number
US07226644B2

Reaction notes

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