Imidazole → Silane, [(9-bromononyl)oxy](1,1-dimethylethyl)dimethyl-

HRID 1670894Notes

Reaction equation

HRID 1670894 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19].N1C=CN=C1>C(Cl)Cl>[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1087001-Nonanol, 9-bromo-

Product 1

HCID 11045996Silane, [(9-bromononyl)oxy](1,1-dimethylethyl)dimethyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl-dimethylsilyl chloride (28.16 g, 186.8 mmol) was added in portions to a solution of 9-bromo-nonan-1-ol (27.8 g, 124.6 mmol) and imidazole (25.4 g, 373 mmol) in dry DCM (400 mL) at −10° C. under a nitrogen atmosphere. The reaction mixture was allowed to warm to RT overnight. The solids were removed by filtration and the filtrate was washed with 10% citric acid (aq), then brine, dried (MgSO4), filtered, and concentrated to dryness to afford the title compound as a yellow oil.

Workup

  1. customThe solids were removed by filtration
  2. washthe filtrate was washed with 10% citric acid (aq)
  3. dry with materialbrine, dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3bdea13b4c9e4a13a3abe82fea508bcb
Source dataset
uspto-grants-2011_08
Patent number
US07994211B2

Reaction notes

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