Imidazole → (3-Bromopropoxy)(tert-butyl)dimethylsilane

HRID 1851074Notes

Reaction equation

HRID 1851074 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][OH:5].[C:6]([Si:10](Cl)([CH3:12])[CH3:11])([CH3:9])([CH3:8])[CH3:7].N1C=CN=C1>>[Br:1][CH2:2][CH2:3][CH2:4][O:5][Si:10]([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:12])[CH3:11]

Participants

4

Reactant 3

HCID 795ImidazoleHCID 123083-Bromo-1-propanolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneYield 93.1%

Procedure

A modified procedure of Galka et al. (J. Lab. Comp. Rad. 2005, 48(11): 797-809) was used to prepare the title compound. A mixture of 3-bromopropanol (39.1 mmole; 5.43 g), tert.-butyldimethylsilylchloride (43.2 mmole; 6.47 g) and imidazole (46.7 mmole; 3.20 g) was stirred at RT for 3 hours under inert gas. The reaction was quenched with water, extracted with diethylether, the organic layer dried over MgSO4, filtered and concentrated. The purification was achieved by column chromatography (PE) to yield the title compound (36.4 mmole; 93%). 1H NMR (300 MHz, CDCl3) 3.73 (t; 3J=5.7 Hz; 2H; CH2O); 3.51 (t; 3J=6.4 Hz; 2H; CH2Br); 2.02 (q; 3J=5.7 Hz; 3J=6.4 Hz; 2H; CH2CH2CH2); 0.89 (s; 9H; C(CH3)3); 0.06 (s; 6H; 2×CH3).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with diethylether
  3. dry with materialthe organic layer dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe purification

Sources & evidence

ORD record
ord-972bb01ff50043298e688b45e2febf15
Source dataset
uspto-grants-2015_02
Patent number
US08957103B2

Reaction notes

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