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

HRID 429362Notes

Reaction equation

HRID 429362 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-2cd206f4601f401cb99a6f5d147406c1
Source dataset
uspto-grants-2001_11
Patent number
US06316466B1

Reaction notes

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