Imidazole → 1-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-4-iodobenzene

HRID 2294959Notes

Reaction equation

HRID 2294959 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[I:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.N1C=CN=C1>ClCCl>[Si:1]([O:16][C:13]1[CH:14]=[CH:15][C:10]([I:9])=[CH:11][CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 108944-IodophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 148035271-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-4-iodobenzeneYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of t-butyl-dimethylsilyl chloride (3.0 g) in dichloromethane (10 ml) was added dropwise to a stirred solution of 4-iodophenol (4.4 g) and imidazole (1.4 g) in dichloromethane (90 ml) whilst maintaining the temperature between 10° C. and 5° C. After the addition was complete, the reaction mixture was stirred for a further 4 hours at ambient temperature. The reaction mixture was washed with water, dried (MgSO4), and evaporated to give 4-(t-butyldimethylsilyloxy)iodobenzene as a colourless oil (6.4 g) NMR(DMSO-d6): 0.0(6H,s), 0.8(9H,s), 6.49-6.58(2H,d), 7.35-7.44(2H,d); m/z=334 (M).

Workup

  1. temperaturewhilst maintaining the temperature between 10° C. and 5° C
  2. additionAfter the addition
  3. washThe reaction mixture was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-1493019790804c75bb20ace5c8b32b36
Source dataset
uspto-grants-1997_11
Patent number
US05691349

Reaction notes

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