Ethyl Acetate → HCID 131730654, compound

HRID 1260125Notes

Reaction equation

HRID 1260125 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[C:12]([CH2:15][O:16][SiH:17]([CH3:19])[CH3:18])[CH:11]=[CH:10]2)([CH3:4])([CH3:3])[CH3:2].[Br:20]Br.C(OC(=O)C)C>ClCCl>[Br:20][C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[C:14]2[C:9]=1[CH:10]=[CH:11][C:12]([CH2:15][O:16][SiH:17]([CH3:19])[CH3:18])=[N:13]2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24408BromineHCID 178504439HCID 178504439, compound

Product 1

HCID 131730654HCID 131730654, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 500 mL flask was added 400 mL dichloromethane and 31.5 g 8-(t-butyl)dimethylsiloxyquinaldine. The mixture was vigorously stirred while 33.14 g bromine (Aldrich) dissolved in 20 mL dichloromethane was added dropwise. The reaction progress was monitored by TLC (5:95 ethylacetate:hexanes). The starting material was found to be completely consumed. Excess bromine was removed by addition of 200 mL of saturated sodium thiosulfate (Aldrich). The organic layer was separated, washed with 150 ml water, 150 ml brine and then dried over MgSO4. After filtering off the salts, the filtrate was concentrated to an oil which was purified by column chromatography, eluting with 20% dichloromethane/hexanes to give 26.04 g of 5-bromo-8-(t-butyl)dimethylsiloxyquinaldine (compound 2ii) as a yellow oil.

Workup

  1. additionwas added dropwise
  2. customto be completely consumed
  3. customExcess bromine was removed by addition of 200 mL of saturated sodium thiosulfate (Aldrich)
  4. customThe organic layer was separated
  5. washwashed with 150 ml water, 150 ml brine
  6. dry with materialdried over MgSO4
  7. filtrationAfter filtering off the salts
  8. concentrationthe filtrate was concentrated to an oil which
  9. customwas purified by column chromatography
  10. washeluting with 20% dichloromethane/hexanes

Sources & evidence

ORD record
ord-459aa679026e4ddc951fe9e5707b73d9
Source dataset
uspto-grants-2013_06
Patent number
US08470208B2

Reaction notes

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