Triethylamine → (3-Bromophenethoxy)(tert-butyl)dimethylsilane

HRID 1278868Notes

Reaction equation

HRID 1278868 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([Br:10])[CH:7]=[CH:8][CH:9]=1.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].CN(C1C=CC=CN=1)C.C(N(CC)CC)C>C(Cl)Cl>[O:1]([CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([Br:10])[CH:7]=[CH:8][CH:9]=1)[Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 27340902-(3-Bromophenyl)ethan-1-ol

Product 1

HCID 11515183(3-Bromophenethoxy)(tert-butyl)dimethylsilaneYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2-hydroxyethyl)bromobenzene (4.0 g, 20 mmol) in methylene chloride (100 ml) at 0° C. was added a solution of tert-butyldimethylsilyl chloride (3.6 g, 24 mmol), dimethylaminopyridine (0.61 g, 5 mmol) and triethylamine (3.6 ml, 25.9 mmol). After 1 h, the reaction mixture was washed with brine, saturated ammonium chloride, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (elution gradient: 0-10% hexane/ethyl acetate) to give 3-(2-tert-butyl-dimethylsiloxyethyl)bromobenzene (6.0 g).

Workup

  1. washthe reaction mixture was washed with brine, saturated ammonium chloride
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography (elution gradient: 0-10% hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ddae750ea58c49d2b0d6509f0d361374
Source dataset
uspto-grants-2002_09
Patent number
US06444696B1

Reaction notes

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