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

HRID 1830637Notes

Reaction equation

HRID 1830637 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.[CH3:13][C:14]([Si:17](Cl)([CH3:19])[CH3:18])([CH3:16])[CH3:15].N1C=CN=C1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:14]([Si:17]([O:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=2)[CH:8]=1)([CH3:19])[CH3:18])([CH3:16])([CH3:15])[CH3:13]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 271446-Bromo-2-naphthalenolHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 134730832-Bromo-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]naphthaleneYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromo-2-naphthol (13.68 g, 61.33 mmol) and TBDMS-Cl (11.09 g, 73.6 mmol) in DMF (50 mL) was added imidazole (10.2 g, 150 mmol). The solution was stirred for 3 hr, mixed with sodium bicarbonate solution (250 mL), and extracted with 50% ethyl acetate-hexanes (3×250 mL). The combined organic layers were washed with water, dried over magnesium sulfate, filtered and evaporation of the solvent yielded a tan oil which was dried under vacuum to yield 19.92 g (97%) of the title compound as a white solid:

Workup

  1. extractionextracted with 50% ethyl acetate-hexanes (3×250 mL)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporation of the solvent
  6. customyielded a tan oil which
  7. customwas dried under vacuum

Sources & evidence

ORD record
ord-6ff2593d2c1f4879a71c7f19f3e3f495
Source dataset
uspto-grants-2006_06
Patent number
US07067524B2

Reaction notes

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