Imidazole → HCID 20519039, compound

HRID 2036248Notes

Reaction equation

HRID 2036248 reaction equation
N1C=CN=C1.[Br:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:17])=[CH:9][CH:8]=1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C=O)C>[Br:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 5756094-bromonaphthalen-1-ol

Product 1

HCID 20519039HCID 20519039, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of imidazole (2.3 g, 34 mmole) and 4-bromonaphthol (13, 5.0 g, 22 mmole) in DMF (10 mL) at 0° C. was added t-butyldimethylsilyl chloride (3.7 g, 24.6 mmole) in several portions. The mixture was warmed to room temperature and stirred for 2 h. The reaction mixture was partitioned between Et2O (500 mL) and water (300 mL) and the aqueous layer was back-extracted with Et2O (300 mL). The combined organic layers were washed with water (300 mL) and brine (300 mL), dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography (silica gel, hexanes) to afford (4-bromonaphthalen-1-yloxy)(tert-butyl)dimethylsilane (14, 6.4 g, 85%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 8.21-8.14 (m, 2H), 7.61-7.49 (m, 3H), 6.74 (d, J=8.2 Hz, 1H), 1.10 (s, 9H), 0.28 (s, 6H).

Workup

  1. customThe reaction mixture was partitioned between Et2O (500 mL) and water (300 mL)
  2. extractionthe aqueous layer was back-extracted with Et2O (300 mL)
  3. washThe combined organic layers were washed with water (300 mL) and brine (300 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (silica gel, hexanes)

Sources & evidence

ORD record
ord-5eca17c809eb408cba1f20a19e86591b
Source dataset
uspto-grants-2013_11
Patent number
US08575176B2

Reaction notes

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