Imidazole → HCID 58764146, compound

HRID 2387066Notes

Reaction equation

HRID 2387066 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([CH2:10][CH3:11])[CH:3]=1.[CH3:12][C:13]([Si:16](Cl)([CH3:18])[CH3:17])([CH3:15])[CH3:14].N1C=CN=C1>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][Si:16]([C:13]([CH3:15])([CH3:14])[CH3:12])([CH3:18])[CH3:17])=[C:4]([CH2:10][CH3:11])[CH:3]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 587642724-Bromo-2-ethylbenzenemethanol

Product 1

HCID 58764146HCID 58764146, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (4-bromo-2-ethyl-phenyl)-methanol in anhydrous DMF was added TBSCl (1.5 eq.) and imidazole (1.5 eq). The mixture was stirred at that temperature for 12 hours before it was diluted with water. The mixture was extracted with Et2O and the combined organic layers were washed with H2O, brine, dried over MgSO4 The solvent was removed in vacuo to give the desired product. (93% yield). 1H NMR (300 MHz, CDCl3): δ 0.09 (s, 6 H), 0.92 (s, 9 H), 1.20 (t, J=7.5 Hz, 3H), 2.57 (q, J=7.5 Hz, 2 H), 4.67 (s, 2 H), 7.29 (s, 3 H).

Workup

  1. extractionThe mixture was extracted with Et2O
  2. washthe combined organic layers were washed with H2O, brine
  3. dry with materialdried over MgSO4 The solvent
  4. customwas removed in vacuo

Sources & evidence

ORD record
ord-4ca6522001914253a73d59f7674f4761
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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