Hydrochloric Acid → HCID 59093118, compound

HRID 1167174Notes

Reaction equation

HRID 1167174 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[CH:3]=1.[H-].[Na+].[F:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18]Br.Cl>CN(C=O)C.CCOCC>[F:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 67968alpha-Bromo-o-fluorotolueneHCID 935522,6-Dihydroxynaphthalene

Product 1

HCID 59093118HCID 59093118, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 15.0 g (94.0 mM) of 2,6-dihydroxynaphthalene in 60 mL of DMF was treated with 3.21 g (80.0 mM) of NaH under nitrogen. The resulting dark solution was treated dropwise with a solution of 5.94 g (31.0 mM) of 2-fluorobenzyl bromide in 20 mL of Et2O over 0.75 h. The mixture was stirred an additional 2 h then treated cautiously with 200 mL 1N HCl. The mixture was stirred 8 to 16 hours then filtered. The solid was washed thoroughly with water and dried. Flash chromatography produced a solid which was recrystallized from i-PrOH to afford 4.51 g (56%) of product as gray crystals mp 143-144° C.

Workup

  1. stirringThe mixture was stirred 8 to 16 hours
  2. filtrationthen filtered
  3. washThe solid was washed thoroughly with water
  4. customdried
  5. customFlash chromatography produced a solid which
  6. customwas recrystallized from i-PrOH

Sources & evidence

ORD record
ord-0b958e5201d14c24a83dc18a81f576c4
Source dataset
uspto-grants-2003_09
Patent number
US06617342B1

Reaction notes

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