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

HRID 1598815Notes

Reaction equation

HRID 1598815 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.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].[SiH3]Cl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 795Imidazole2×HCID 271446-Bromo-2-naphthalenolHCID 28928tert-Butyldimethylsilyl chlorideHCID 61622Chlorosilane

Product 1

HCID 134730832-Bromo-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]naphthaleneYield 74.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Bromo-2-naphthol (10 g, 44 mmol), imidazole (7.4 g, 110 mmol), and t-butyldimethylsilyl chloride (10 g, 66 mmol) were stirred in DMF (50 mL) at room temperature overnight. TLC analysis indicated incomplete reaction, so additional imidazole (0.6 g) and silyl chloride (1.3 g) were added, and stirring continued 1 day. After evaporation of DMF, the mixture was extracted with EtOAc and 5% aqueous KHSO4, dried (Na2SO4), and evaporated. The crude product was purified by silica gel chromatography, eluting with hexane, to yield a colorless solid (11 g). mp 62°-63° C. 1H NMR (300 MHz, CDCl3): 7.90 (d, 1H, J=l Hz), 7.62 (d, 1H, J=9 Hz), 7.55 (d, 1H, J=9 Hz), 7.46 (dd, 1H, J=9, 2 Hz), 7.14 (d, 1H, J=2 Hz), 7.08 (dd, 1H, J=9,2 Hz), 1.00 (s, 9H), 0.23 (s, 6H). MS(CH4): 365 (20%, M+C2H5, 1 Br isotope pattern), 337 (base, M+H, 1 Br isotope pattern).

Workup

  1. customreaction
  2. customAfter evaporation of DMF
  3. extractionthe mixture was extracted with EtOAc and 5% aqueous KHSO4
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with hexane

Sources & evidence

ORD record
ord-39f09252476a4496a6fca5975261e145
Source dataset
uspto-grants-1998_04
Patent number
US05739163

Reaction notes

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