Imidazole → 6-methylnaphthalen-2-ol

HRID 2271266Notes

Reaction equation

Br[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.[Si](Cl)(C(C)(C)C)(C)[CH3:14].N1C=CN=C1.[Li]CCCC.CI>>[CH3:14][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

Participants

Reactant 5

HCID 795Imidazole

HCID 6328Methyl iodide

HCID 271446-Bromo-2-naphthalenol

HCID 28928tert-Butyldimethylsilyl chloride

HCID 178418339Butyllithium

Product 1

HCID 2428346-methylnaphthalen-2-ol

Procedure

React 6-bromo-2-naphthol with t-butyl dimethylsilyl chloride and imidazole, followed by adding n-BuLi and CH3I. Deprotect the hydroxyl group by reacting with n-Bu4F to produce the title compound.

Sources & evidence

ORD record: ord-e48013da5b4941b6aae10650e48bef19
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06333435B1

Reaction notes

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