Imidazole → [(4-Bromo-2-thienyl)methoxy]t-butyldimethylsilane

HRID 1809087Notes

Reaction equation

HRID 1809087 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][OH:8])[S:5][CH:6]=1.[Si:9](Cl)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].N1C=CN=C1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2795484(4-Bromo-2-thienyl)methanol

Product 1

HCID 10614666[(4-Bromo-2-thienyl)methoxy]t-butyldimethylsilane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-bromo-thiophen-2-yl)-methanol (13.2 g, 72 mmol) in DCM (140 mL) was added t-butyldimethylsilyl chloride (79.2 mmol) and imidazole (79.2 mmol). The reaction was stirred for 1 hour, then quenched with 1 M HCl and extracted into DCM. The organic solution was dried over magnesium sulphate, filtered and the solvent removed to give the title compound as a yellow oil, which was used without further purification.

Workup

  1. customquenched with 1 M HCl
  2. extractionextracted into DCM
  3. dry with materialThe organic solution was dried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent removed

Sources & evidence

ORD record
ord-08ae7bdb24ff492485dde68d30ee6107
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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