Imidazole → (4-Bromo-phenoxy)-triisopropylsilane

HRID 1815992Notes

Reaction equation

HRID 1815992 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.N1C=CN=C1.[CH:14]([Si:17](Cl)([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])([CH3:16])[CH3:15]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][Si:17]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:14]([CH3:16])[CH3:15])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 78084-BromophenolHCID 139400Triisopropylsilyl chloride

Product 1

HCID 536194(4-Bromo-phenoxy)-triisopropylsilaneYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromophenol (17.3 g, 100 mmole) in dry DMF (100 mL) at RT was added imidazole (13.62 g, 200 mmole), followed by triisopropylsilyl chloride (22.5 mL, 105 mmole). After 4 hr the mixture was diluted with H2O (50 mL) and extracted with hexanes (3×75 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound (32.23 g, 100%) as a clear oil which was used without purification: 1H NMR (300 MHz, CDCl3) δ 7.29 (d, J=6 Hz, 2 H), 6.71 (d, J=6 Hz, 2 H), 1.22 (m, 3 H), 1.09 (m, 18 H).

Workup

  1. extractionextracted with hexanes (3×75 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4a978fdc0b11409d86a0bb8e77a20fef
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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