Imidazole → ({4'-Bromo-[1,1'-biphenyl]-4-yl}oxy)(tert-butyl)dimethylsilane

HRID 481999

Reaction equation

HRID 481999 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1.N1C=CN=C1.C(OCC)C>CN(C)C=O>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:18][CH:17]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 950934-Bromo-4'-hydroxybiphenyl

Product 1

HCID 3765121({4'-Bromo-[1,1'-biphenyl]-4-yl}oxy)(tert-butyl)dimethylsilaneYield 88.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyldimethylsilyl chloride (1.8 g) was added over 30 minutes to a stirred solution of 4-bromo-4'-hydroxybiphenyl (2.49 g) and imidazole (1.63 g) in dimethylformamide (15 ml) whilst keeping the temperature of the reaction mixture below 10° C. The reaction mixture was stirred at room temperature for 18 hours. Diethyl ether (225 ml) was added, the ether washed with saturated sodium hydrogen carbonate solution (3×60 ml) and brine (100 ml), dried (MgSO4) and evaporated to yield, as a colourless oil, 4-bromo-4'-(tert-butyldimethylsilyloxy)biphenyl (3.2 g); NMR (CDCl3): 0.2(6H, s), 1.0(9H, s), 6.8-6.9(2H, d), 7.3-7. 4(4H, m) and 7.45-7.55(2H, d).

Workup

  1. customthe temperature of the reaction mixture below 10° C
  2. washthe ether washed with saturated sodium hydrogen carbonate solution (3×60 ml) and brine (100 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-b0990df56b714f7a96ecf25dd8db54d2
Source dataset
uspto-grants-1998_08
Patent number
US05792777

Linked notes

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