Imidazole → (1-Bromo-naphthalen-2-yloxy)-triisopropyl-silane

HRID 1814335Notes

Reaction equation

HRID 1814335 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:12].[CH:13]([Si:16](Cl)([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])([CH3:15])[CH3:14].N1C=CN=C1.N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl.O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][Si:16]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:13]([CH3:15])[CH3:14]

Participants

8

Reactant 4

HCID 795ImidazoleHCID 1049PyridineHCID 113161-Bromo-2-naphtholHCID 139400Triisopropylsilyl chloride

Product 1

HCID 22504240(1-Bromo-naphthalen-2-yloxy)-triisopropyl-silaneYield 99.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1-Bromo-2-naphthol (5.00 g, 22.4 mmol) was mixed with triisopropylsilyl chloride (7.2 mL, 33.6 mmol), DMAP (402 mg, 3.30 mmol), imidazole (3.81 g, 56.0 mmol), and pyridine (6 mL) in CH2Cl2 (50 mL). The reaction was refluxed for two hours. TLC analysis (silica, 15% EtOAc-hexanes) indicated the reaction was complete. The reaction was allowed to cool to room temperature and then was diluted with H2O. The dilution was extracted three times with CH2Cl2. The organic extracts were combined, washed with brine solution, dried over Na2SO4, filtered through celite, and concentrated. The crude product was purified by flash chromatography (SiO2, 100% hexanes) to give (1-bromo-naphthalen-2-yloxy)-triisopropyl-silane (8.4 g, 22.2 mmol) as a colorless oil in 99% yield. 1H NMR (300 MHz) CDCl3 8.21 (d, J=7.5 Hz, 1H), 7.76 (d, J=8.5 Hz, 1H), 7.68 (d, J=8.8 Hz, 1H), 7.54 (m, 1H), 7.38 (m, 1H), 7.15 (d, J=8.8 Hz, 1H), 1.38 (m, 3H), 1.16 (d, J=7.1 Hz, 18H).

Workup

  1. temperatureThe reaction was refluxed for two hours
  2. extractionThe dilution was extracted three times with CH2Cl2
  3. washwashed with brine solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered through celite
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (SiO2, 100% hexanes)

Sources & evidence

ORD record
ord-cc6ac67d4e814cdcaac13c3e119f2ed4
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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