4-Methoxybenzyl alcohol → HCID 18545246, compound

HRID 564869Notes

Reaction equation

HRID 564869 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]([Cl: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]([Cl:21])[CH:15]=1

Participants

5

Reactant 3

HCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 27362231-Bromo-3-chloro-5-fluorobenzene

Product 1

HCID 18545246HCID 18545246, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a mixture of 5.8 ml of p-methoxybenzyl alcohol and 90 ml of N-methylpyrrolidone was added 2.13 g 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 9.3 g of 1-bromo-3-chloro-5-fluorobenzene, followed by stirring at 50° C. for 3 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 13.2 g of the title compound.

Workup

  1. stirringby stirring at 50° C. for 3 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-a2fc2731f43e41e69ed2f8a5447eaf64
Source dataset
uspto-grants-2001_01
Patent number
US06169086A

Reaction notes

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