Chlorosuccinimide → Tert-butyl(2-(5-chlorothiophen-2-yl)ethoxy)dimethylsilane

HRID 1689531Notes

Reaction equation

HRID 1689531 reaction equation
[Cl:1]N1C(=O)CCC1=O.[C:9]([Si:13]([CH3:23])([CH3:22])[O:14][CH2:15][CH2:16][C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)([CH3:12])([CH3:11])[CH3:10]>C(Cl)(Cl)Cl.C(Cl)Cl>[C:9]([Si:13]([O:14][CH2:15][CH2:16][C:17]1[S:18][C:19]([Cl:1])=[CH:20][CH:21]=1)([CH3:23])[CH3:22])([CH3:10])([CH3:12])[CH3:11]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 22503634Tert-butyldimethyl(2-(thiophen-2-YL)ethoxy)silane

Product 1

HCID 57989349Tert-butyl(2-(5-chlorothiophen-2-yl)ethoxy)dimethylsilane

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

N-chlorosuccinimide (0.83 g) was added portionwise to a solution of tert-butyldimethyl(2-(thiophen-2-yl)ethoxy)silane (1.5 g) (example 4 step a) in chloroform (50 mL) and heated to reflux for 3 days. The yellow solution was diluted with DCM (100 mL) and washed with saturated sodium bicarbonate solution (2×100 mL), brine (100 mL), dried over sodium sulphate, filtered and evaporated in vacuo. The residue was purified by silica gel chromatography eluting with iso-hexane. The fractions containing product were combined and evaporated in vacuo to give the subtitled compound as a clear oil. Yield 1 g.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 days
  3. washwashed with saturated sodium bicarbonate solution (2×100 mL), brine (100 mL)
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with iso-hexane
  9. additionThe fractions containing product
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-91a98baad1104eb7806c67b147667c58
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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