Imidazole → 2-Bromo-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]naphthalene

HRID 917685Notes

Reaction equation

HRID 917685 reaction equation
[Br: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.N1C=CN=C1.[C:18]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])([CH3:20])[CH3:19].CCCCCC>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][Si:22]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:24])[CH3:23])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8058HexaneHCID 271446-Bromo-2-naphthalenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 134730832-Bromo-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]naphthaleneYield 52.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

200 g 6-bromonaphthalen-2-ol, 143 g imidazole and 151 g tert.-butylchlorodimethylsilane were dissolved in 1,000 ml dimethylformamide, stirred for two hours at ambient temperature, the solution largely concentrated (506 g), the residue dissolved in ethyl acetate and water, 1,500 ml saturated sodium chloride solution added, the phases separated, the aqueous phase extracted twice with ethyl acetate and the organic phases combined and concentrated. The crude product obtained was dissolved in boiling hexane and subsequently kept overnight at 4° C. After filtration, 158 g (6-bromonaphthalen-2-yloxy)-tert.-butyldimethylsilane were isolated. Repeated concentration of the mother liquor and recrystallisation from methanol yielded a further 54 g (6-bromonaphthalen-2-yloxy)-tert.-butyldimethylsilane.

Workup

  1. concentrationthe solution largely concentrated (506 g)
  2. dissolutionthe residue dissolved in ethyl acetate
  3. additionwater, 1,500 ml saturated sodium chloride solution added
  4. customthe phases separated
  5. extractionthe aqueous phase extracted twice with ethyl acetate
  6. concentrationconcentrated
  7. customThe crude product obtained
  8. dissolutionwas dissolved
  9. customat 4° C
  10. filtrationAfter filtration

Sources & evidence

ORD record
ord-c4991e4714c94fda898cb76448ec9588
Source dataset
uspto-grants-2007_09
Patent number
US07273952B2

Reaction notes

Loading…