Imidazole → [(6-Bromonaphthalen-2-yl)oxy](tert-butyl)dimethylsilane

HRID 259790

Reaction equation

HRID 259790 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 13473083[(6-Bromonaphthalen-2-yl)oxy](tert-butyl)dimethylsilaneYield 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-a5d80d7583b246718f86a6891c700862
Source dataset
uspto-grants-1996_06
Patent number
US05523302

Linked notes

Loading…