Imidazole → [4-(3-Bromophenyl)butoxy](tert-butyl)diphenylsilane

HRID 916841Notes

Reaction equation

HRID 916841 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][CH:7]=1.N1C=CN=C1.[Si:18](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][Si:18]([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 218954894-(3-Bromophenyl)butan-1-ol

Product 1

HCID 69439190[4-(3-Bromophenyl)butoxy](tert-butyl)diphenylsilane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(3-bromophenyl)butan-1-ol (5 g) (WO 0266422 A1) in dry DMF was treated with imidazole (1.8 g) and tert-butyldiphenylsilyl chloride (7.2 g) and stirred at room temperature for 16 h. The reaction mixture was partitioned between water and EtOAc. The organic phase was washed with 2M HCl, water, sat. NH4Cl(aq), water, dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography (SPE, Gradient between cyclohexane and cyclohexane-EtOAc (5:1) to give the title compound. LCMS RT=4.82 min

Workup

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. washThe organic phase was washed with 2M HCl, water, sat. NH4Cl(aq), water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (SPE, Gradient between cyclohexane and cyclohexane-EtOAc (5:1)

Sources & evidence

ORD record
ord-d89f6722d1e44d8db50bb40007166e13
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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