Imidazole → [4-(Bromomethyl)-phenoxy][tris(1-methylethyl)]silane

HRID 2400545Notes

Reaction equation

HRID 2400545 reaction equation
[CH3:1][CH:2]([Si:4]([CH:17]([CH3:19])[CH3:18])([CH:14]([CH3:16])[CH3:15])[O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12]O)=[CH:8][CH:7]=1)[CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[Br:44]Br.C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OCC)C.C(#N)C.O>[Br:44][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][Si:4]([CH:17]([CH3:19])[CH3:18])([CH:14]([CH3:16])[CH3:15])[CH:2]([CH3:3])[CH3:1])=[CH:7][CH:8]=1

Participants

9

Reactant 5

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 13097Triphenylphosphine OxideHCID 24408BromineHCID 59504706(4-((Triisopropylsilyl)oxy)phenyl)methanol

Product 1

HCID 44134296[4-(Bromomethyl)-phenoxy][tris(1-methylethyl)]silane

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (4-{[tris(1-methylethyl)silyl]oxy}phenyl)methanol (Step 2, 1.0 g, 3.56 mmol) in diethyl ether (20 mL) and acetonitrile (7.5 mL) was added triphenylphosphine (0.94 g, 3.57 mmol) and imidazole (243 mg, 3.57 mmol). After being cooled to 0° C., a solution of bromine (184 μL, 3.56 mmol) in diethyl ether (2.5 mL) was added dropwise. The reaction mixture was stirred at rt over night. Then water was added, and it was extracted with ethyl acetate. The organic extract was washed with water and brine, dried over anhydrous magnesium sulfate and filtered. After evaporation of the solvent, the crude material was treated with pentane. Precipitated triphenylphosphine oxide (TPPO) was removed by filtration. The solvent was evaporated in vacuo. The product thus obtained (1.42 g) still contained some TPPO (as judged by tlc) but was used for subsequent reactions without further purification.

Workup

  1. extractionit was extracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customAfter evaporation of the solvent
  7. additionthe crude material was treated with pentane
  8. customPrecipitated triphenylphosphine oxide (TPPO) was removed by filtration
  9. customThe solvent was evaporated in vacuo
  10. customThe product thus obtained (1.42 g)
  11. customwas used for subsequent reactions without further purification

Sources & evidence

ORD record
ord-9ef4a0b986f84a4bb9b0848133024da8
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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