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

HRID 733654Notes

Reaction equation

HRID 733654 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. Yield: 1.36 g (80%), white crystals. 1H-NMR (CDCl3) □ 0.08 (s, 6H), 1.06 (s, 9H), 7.08 (dd, 1H), 7.15 (s, 1H), 7.47 (dd, 1H), 7.56 (d, 1H), 7.64 (d, 1H), 7.92 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-c1ad0f51669d4a8d9f5a4a33caf9cd67
Source dataset
uspto-grants-2009_09
Patent number
US07589239B2

Reaction notes

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