HCID 23114001, compound → HCID 23113841, compound

HRID 2376357Notes

Reaction equation

HRID 2376357 reaction equation
Br[CH:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]1([O:10][CH2:11][CH2:12]Cl)C.[CH2:14]([Li])CCC>C1COCC1>[CH3:14][C:7]1[C:2]2[CH2:12][CH2:11][O:10][C:3]=2[CH:4]=[C:5]([CH3:8])[CH:6]=1

Participants

4

Reactant 2

HCID 23114001HCID 23114001, compoundHCID 178418339Butyllithium

Product 1

HCID 23113841HCID 23113841, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-bromo-2-(2-chloroethoxy)-2,4-dimethylbenzene obtained in Reference Example 217 (8.70 g, 33.0 mmol) in THF (210 mL) was quickly added n-butyllithium (1.6 M hexane solution, 31 mL, 49.5 mmol) under argon atmosphere at 0° C., and the mixture was stirred for 30 minutes. The reaction solution was warmed to room temperature, to which ice was added, which was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, was filtered, and then was concentrated under reduced pressure to obtain 4.70 g (yield 96%) of the title compound. Oily matter.

Workup

  1. customat 0° C.
  2. additionwas added
  3. extractionwhich was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationwas filtered
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-2dd622b5766e4de48f50615f51b182ce
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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