Imidazole → (5-Bromomethyl-3-methoxy-thiophen-2-ylmethoxy)-tert-butyl-dimethyl-silane

HRID 69093Notes

Reaction equation

HRID 69093 reaction equation
[Br:1][CH2:2][C:3]1[S:7][C:6]([CH2:8][OH:9])=[C:5]([O:10][CH3:11])[CH:4]=1.N1C=CN=C1.[C:17]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])([CH3:19])[CH3:18]>ClCCl>[Br:1][CH2:2][C:3]1[S:7][C:6]([CH2:8][O:9][Si:21]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:23])[CH3:22])=[C:5]([O:10][CH3:11])[CH:4]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 67235638HCID 67235638, compound

Product 1

HCID 68194046(5-Bromomethyl-3-methoxy-thiophen-2-ylmethoxy)-tert-butyl-dimethyl-silaneYield 102.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-bromomethyl-3-methoxy-thiophen-2-yl)-methanol (0.6 g, 2.5 mmol) in anhydrous dichloromethane (10 mL) is added imidazole (0.516 g, 7.59 mmol) and tert-butylchlorodimethylsilane (0.412 g, 2.75 mmol) at 0° C. The reaction mixture is allowed to warm to room temperature and stirred for 1 hour. The reaction mixture is quenched with water and concentrated. The residue is dissolved in DCM, washed with water (25 mL) and brine (25 mL), dried over Na2SO4, filtered, and concentrated to give the title compound (0.9 g). ESI/MS m/z (79Br/81Br) 351/353.1 [M+H]+.

Workup

  1. customThe reaction mixture is quenched with water
  2. concentrationconcentrated
  3. dissolutionThe residue is dissolved in DCM
  4. washwashed with water (25 mL) and brine (25 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fbb95f0cfbd340b5888b3b91d2f27435
Source dataset
uspto-grants-2014_09
Patent number
US08822486B2

Reaction notes

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