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

HRID 2065063Notes

Reaction equation

HRID 2065063 reaction equation
N#N.[Br:3][C:4]1[CH:5]=[C:6]([CH2:9][OH:10])[S:7][CH:8]=1.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1>C(Cl)Cl.O>[Br:3][C:4]1[CH:5]=[C:6]([CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[S:7][CH:8]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 947NitrogenHCID 28928tert-Butyldimethylsilyl chlorideHCID 2795484(4-Bromo-2-thienyl)methanol

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), (4-bromo-thiophen-2-yl)-methanol (3.97 g, 20.57 mmol) was dissolved in dry CH2Cl2 (50 mL). tert-Butyldimethylsilyl chloride (3.59 g, 22.63 mmol) was added at rt followed by imidazole (1.56 g, 22.63 mmol). The reaction mixture was stirred at rt for 1 h. Water was added, the layers were separated and the org. layer was dried over MgSO4, filtered, and the solvent removed under reduced pressure. Purification of the residue by FC (hept) gave the title compound as a colorless oil. TLC: rf (100:1 hept-EA)=0.44. LC-MS-conditions 02: tR=1.21 min.

Workup

  1. customthe layers were separated
  2. dry with materiallayer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customPurification of the residue by FC (hept)

Sources & evidence

ORD record
ord-d4959b0a2b004b81953a2bc6ec996e29
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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