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Imidazole → 4-Bromophenyl-tert-butyldimethylsilyl ether

HRID 1037
Notes
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Reaction equation

HRID 1037 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](O)=[CH:4][CH:3]=1.N1[CH:13]=[CH:12]N=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].[OH2:22]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:15][Si:14]([O:22][Si:14]([CH2:16][C:13]2[CH:12]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)([CH3:15])[C:17]([CH3:20])([CH3:19])[CH3:18])([C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:16])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 78084-BromophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 688013174-Bromophenyl-tert-butyldimethylsilyl ether

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Procedure

4-Bromophenol (5.76 g, 30 mmol), imidazole (4.08 g, 60 mmol) and tert-butyldimethylsilyl chloride (5.02 g, 33 mmol) were stirred in anhydrous DMF (100 mL) at 25° C. for 18 h. The reaction mixture was then poured into water (100 mL) and extracted with ethyl acetate (2×75 mL). The combined extracts were washed with water (2×75 mL), brine (75 mL) and dried (MgSO4) before concentration in vacuo. The crude product was purified using "flash" silica gel column chromatography with ethyl acetate:hexane (1:4) as eluant to afford the title compound as an oil, 7.9 g, 92%. 1H NMR (CDCl3, 300 MHz): δ 7.33 (app. dt, J=9, 3, 1 Hz, 2 H), 6.73 (app. dt, J=9, 3, 1 Hz, 2 H) 0.98 (s, 9 H),0.21 (s, 6 H).

Workup

  1. extractionextracted with ethyl acetate (2×75 mL)
  2. washThe combined extracts were washed with water (2×75 mL), brine (75 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationbefore concentration in vacuo
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-d98a159036ee4b80b53a751599758e27
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723477

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes