1,2-Dibromoethane → HCID 18702787, compound

HRID 2287941Notes

Reaction equation

HRID 2287941 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]=1.[CH2:12]([Li])[CH2:13][CH2:14][CH3:15].Br[CH2:18][CH2:19]Br>C1COCC1.CCCCCC>[CH3:1][O:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([CH2:15][CH2:14][CH:13]2[C:12]3[C:4](=[CH:5][CH:6]=[CH:18][CH:19]=3)[C:3]([O:2][CH3:1])=[CH:11]2)[CH:4]=1

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 27530713-methoxy-1H-indeneHCID 178418339Butyllithium

Product 1

HCID 18702787HCID 18702787, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
50 °C

Procedure

10.9 g (75 mmol) of 3-methoxyindene (prepared as described in J. Am. Chem. Soc. 106 (1984) 6702) were dissolved in 100 ml of THF, and 47 ml (75.2 mmol) of a 1.6 M butyllithium solution in hexane were added. The mixture was stirred at 50° C. for 2 hours, 3.25 ml (30.1 mmol) of 1,2-dibromoethane in 30 ml of THF were added dropwise at -78° C., and the mixture was warmed to room temperature. The solvent was stripped off, and the product was extracted with toluene. Yield 6.2 g (64%).

Workup

  1. temperaturethe mixture was warmed to room temperature
  2. extractionthe product was extracted with toluene

Sources & evidence

ORD record
ord-ed0d63da0cfd4b18a81ebae8e33eb4f8
Source dataset
uspto-grants-2000_07
Patent number
US06087292

Reaction notes

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