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

HRID 915725Notes

Reaction equation

HRID 915725 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[CH:3]=1.N1C=CN=C1.[CH3:18][C:19]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])[CH3:20].O>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][Si:22]([C:19]([CH3:21])([CH3:20])[CH3:18])([CH3:24])[CH3:23])[CH:8]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 271446-Bromo-2-naphthalenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 134730832-Bromo-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]naphthaleneYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-6-hydroxynaphthalene (100.0 g, 0.45 mol) and imidazole (75.0 g, 1.10 mol) were dissolved in 300 mL of DMF. To this solution was added TBDMS-Cl (80.0 g, 0.53 mol). The reaction was stirred at room temperature under nitrogen overnight. The reaction was poured into water, and the precipitate was filtered, washed with water and cold ethanol. The crude product was recrystallized from ethanol to give 97.2 g of off-white crystals (64% yield). 1H NMR (CDCl3) δ ppm: 0.24 (s, 6H), 1.01 (s, 9H), 7.07 (dd, J1=8.8 Hz, J2=2.3 Hz, 1H), 7.14 (s, 1H), 7.45 (dd, J1=8.8 Hz, J2=2.3 Hz, 1H), 7.53 (d, J=8.8 Hz, 1H), 7.60 (d, J=8.8 Hz, 1H), 7.90 (s, 1H). 13C NMR (CDCl3) δ ppm: −4.34, 18.24, 25.68, 114.86, 117.26, 123.05, 128.29, 128.42, 129.39, 129.57, 130.24, 133.04. Mp 62-64° C. FD-MS: 337 (M+).

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with water and cold ethanol
  3. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-1271c172ac74439d9105affaed2d4d14
Source dataset
uspto-grants-2007_09
Patent number
US07267892B2

Reaction notes

Loading…