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

HRID 2377222Notes

Reaction equation

HRID 2377222 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.[CH3:18][C:19]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])[CH3:20]>C1COCC1.CCOCC>[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)[Si:22]([C:19]([CH3:21])([CH3:20])[CH3:18])([CH3:24])[CH3:23]

Participants

6

Reactant 3

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

Product 1

HCID 134730832-Bromo-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]naphthalene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-2-napthol (1.12 g, 5 mmol) in anhydrous THF (15 mL) was added imidazole (0.476 g, 7 mmol) followed by TBSCl (1.05 g, 7 mmol) at room temperature under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 40 h and was diluted with ether, washed with brine and dried over anhydrous Mg2SO4. The solvent was removed to yield the crude product, which was recrystallized from methanol.

Workup

  1. washwashed with brine
  2. dry with materialdried over anhydrous Mg2SO4
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-07a76a0bdcdc47bb9b75b2c289f44651
Source dataset
uspto-grants-2008_12
Patent number
US07468462B2

Reaction notes

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