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

HRID 843066Notes

Reaction equation

HRID 843066 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-668967718dff4f88a743e91da82d11cf
Source dataset
uspto-grants-2002_04
Patent number
US06376527B1

Reaction notes

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