Imidazole → 3-(4-Bromophenyl)propoxy-tert-butyl-dimethylsilane

HRID 561842Notes

Reaction equation

HRID 561842 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.N1C=CN=C1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][O:11][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 105606143-(4-Bromophenyl)propan-1-ol

Product 1

HCID 153429623-(4-Bromophenyl)propoxy-tert-butyl-dimethylsilane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(4-bromophenyl)propan-1-ol (1 eq.) in DMF (0.25 M) was added imidazole (1.2 eq.) and tert-butyldimethylsilyl chloride (1.1 eq.). The resulting solution was stirred at RT for 13 h. The reaction mixture was quenched with sat. aq. NH4Cl and extracted with hexanes. The combined organic extracts were washed further with water and brine. Concentration of the organic extracts in vacuo afforded the title compound as a colorless oil.

Workup

  1. customThe reaction mixture was quenched with sat. aq. NH4Cl
  2. extractionextracted with hexanes
  3. washThe combined organic extracts were washed further with water and brine

Sources & evidence

ORD record
ord-3206a52306894a0096c1bc1aaac027a6
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

Loading…