4-Methoxybenzyl alcohol → HCID 18545377, compound

HRID 564868Notes

Reaction equation

HRID 564868 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][OH:10])=[CH:7][CH:8]=1.[H-].[Na+].[Br:13][C:14]1[CH:19]=[C:18](F)[CH:17]=[C:16]([F:21])[CH:15]=1>CN1CCCC1=O>[Br:13][C:14]1[CH:19]=[C:18]([O:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:17]=[C:16]([F:21])[CH:15]=1

Participants

5

Reactant 3

HCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 1363131-Bromo-3,5-difluorobenzene

Product 1

HCID 18545377HCID 18545377, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a mixture of 2.2 ml of p-methoxybenzyl alcohol and 50 ml of N-methylpyrrolidone was added 840 mg of sodium hydride (60% oil dispersion), and the resulting mixture was stirred at room temperature for 45 minutes in a nitrogen atmosphere. To the reaction mixture was added 2 ml of 1-bromo-3,5-difluorobenzene, followed by stirring at 50° C. for 1.5 hours. The reaction mixture was poured into 50 ml of ice-diluted hydrochloric acid and extracted three times with diethyl ether-hexane (1:1 by volume. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography using a hexane-ethyl acetate (19:1 by volume) mixed solvent. The fraction containing the desired compound was concentrated to furnish 4.88 g of the title compound.

Workup

  1. stirringby stirring at 50° C. for 1.5 hours
  2. extractionextracted three times with diethyl ether-hexane (1:1 by volume
  3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography
  7. additionmixed solvent
  8. additionThe fraction containing the desired compound
  9. concentrationwas concentrated

Sources & evidence

ORD record
ord-68b678b8b74a41adbd6b9226cc46d107
Source dataset
uspto-grants-2001_01
Patent number
US06169086A

Reaction notes

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