Imidazole → Tert-butyl(3,5-dibromophenoxy)dimethylsilane

HRID 1969182Notes

Reaction equation

HRID 1969182 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([Br:8])[CH:7]=1.N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>ClCCl.C(OCC)C>[C:18]([Si:15]([O:9][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[C:6]([Br:8])[CH:5]=1)([CH3:17])[CH3:16])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 122803,5-DibromophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 21762106Tert-butyl(3,5-dibromophenoxy)dimethylsilane

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

3,5-Dibromophenol (59.6 mmol; 15 g) and imidazole (65.5 mmol; 4.5 g) were dissolved in dichloromethane (150 mL) and tert-butyl-dimethylsilylchloride (65.5 mmol; 9.9 g) was added. The reaction mixture was stirred at room temperature for 16 hours, diluted with diethyl ether, and filtered. The organic solution was washed with saturated ammonium chloride, saturated sodium hydrogen carbonate, and water and dried and evaporated to dryness. Yield: 22 g. HPLC-MS: m/z: 366.9 (M+); Rt: 3.09 min.

Workup

  1. filtrationfiltered
  2. washThe organic solution was washed with saturated ammonium chloride, saturated sodium hydrogen carbonate, and water
  3. customdried
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-904abfd161bc415986362bf946478ddd
Source dataset
uspto-grants-2013_04
Patent number
US08426473B2

Reaction notes

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