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

HRID 1715387Notes

Reaction equation

HRID 1715387 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.[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C=O)C.CCCCCCC.[NH4+].[Cl-]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][O:11][Si:21]([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22])=[CH:6][CH:7]=1

Participants

7

Reactant 3

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

Product 1

HCID 153429623-(4-Bromophenyl)propoxy-tert-butyl-dimethylsilaneYield 90%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8900HeptaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A sol. of 3-(4-bromo-phenyl)-propan-1-ol (49.4 g, 230 mmol) in DMF (500 mL) is cooled to 0° C., and imidazole (23.77 g, 349 mmol) and TBDMS-Cl (52.6 g, 349 mmol) are added. The mixture is stirred overnight, while warming up to rt. The mixture is diluted with heptane (1.0 L) and aq. sat. NH4Cl (800 mL), and the mixture is shaken. The layers are separated. The aq. layer is extracted with heptane, and the combined org. extracts are washed with brine. The org. extracts are dried over MgSO4, filtered, and the solvents are removed under reduced pressure. Purification by FC (Et2O/heptane 1:99→1:19) yields the title compound (68.1 g, 90%). LC-MS: tR=1.24 min.

Workup

  1. stirringthe mixture is shaken
  2. customThe layers are separated
  3. extractionThe aq. layer is extracted with heptane
  4. washextracts are washed with brine
  5. dry with materialextracts are dried over MgSO4
  6. filtrationfiltered
  7. customthe solvents are removed under reduced pressure
  8. customPurification by FC (Et2O/heptane 1:99→1:19)

Sources & evidence

ORD record
ord-5a573c7ff4244d1f9896e60ee39985e9
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

Loading…