Imidazole → (6-Bromohexyloxy)-tert-butyldimethylsilane

HRID 1944855Notes

Reaction equation

HRID 1944855 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21]>C(Cl)Cl>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 779706-Bromo-1-hexanol

Product 1

HCID 4260352(6-Bromohexyloxy)-tert-butyldimethylsilaneYield 106.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Imidazole (1.1 g, 16.56 mmol) and TBS-Cl (1.37 g, 9.11 mmol) were added to a stirring solution of 6-bromohexanol (1.5 g, 8.28 mmol) in CH2Cl2 (80 mL). The resulting mixture was stirred over night then quenched with H2O (100 mL). The aqueous layer was extracted with CH2Cl2 (3×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give the title compound (2.6 g) as clear oil. The compound was used with no further purification.

Workup

  1. customthen quenched with H2O (100 mL)
  2. extractionThe aqueous layer was extracted with CH2Cl2 (3×50 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9e6dd28518af4c2180b488639ba303c5
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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