Dichloromethane → (2-Bromoethoxy)-tert-butyldimethylsilane

HRID 1474603Notes

Reaction equation

HRID 1474603 reaction equation
[Br:1][CH2:2][CH2:3][OH:4].C(Cl)Cl.[C:8]([Si:12](Cl)([CH3:14])[CH3:13])([CH3:11])([CH3:10])[CH3:9]>C(OC(=O)C)C>[Br:1][CH2:2][CH2:3][O:4][Si:12]([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 108982-BromoethanolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneYield 77.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromoethanol (3.4 mL, 48.34 mmol) in dry DCM (25 mL) imidazole (9.86 g, 143 mmol) and tert-butylchlorodimethylsilane (10.9 gm, 72.52 mmol) were added at 0° C. The reaction mixture was stirred at r.t. for 24 h. After completion of reaction, as confirmed by TLC, the reaction mixture was diluted with ethylacetate (350 mL) and washed with water (4×20 mL). The organic layer was dried over anhydrous Na2SO4 and volatiles were evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, 0.2:9.8 Ethyl acetate:Pet. Ether) to afford title compound (204 mg, 77.5%) as liquid.

Workup

  1. customAfter completion of reaction
  2. washwashed with water (4×20 mL)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4 and volatiles
  4. customwere evaporated in vacuo
  5. customThe residue obtained
  6. customwas purified by column chromatography (silica gel, 0.2:9.8 Ethyl acetate:Pet. Ether)

Sources & evidence

ORD record
ord-6a1b79667c964a5893bb715df868ffa1
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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