Dibenzofuran → 1-Bromodibenzofuran

HRID 1509770Notes

Reaction equation

HRID 1509770 reaction equation
CCCCCC.C([Li])CCC.C1COCC1.[CH:17]1[C:25]2[C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[O:22][C:21]=2[CH:20]=[CH:19][CH:18]=1.[Br:30]CCBr>O>[Br:30][C:17]1[C:25]2[C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[O:22][C:21]=2[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 568DibenzofuranHCID 78391,2-DibromoethaneHCID 8028TetrahydrofuranHCID 178418244HCID 178418244, compound

Product 1

HCID 1905421-Bromodibenzofuran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under nitrogen current at −78° C., an n-butyl lithium hexane solution (1.6M, 69 ml) is dropped to a THF solution (175 ml) containing 16.82 g of dibenzofuran, and the temperature of the mixture is raised to room temperature over 80 minutes. The obtained solution is again cooled to −78° C., 19.0 ml of 1,2-dibromoethane is added to the solution, and the temperature of the solution is raised to room temperature over 120 minutes. Water is added to the obtained reaction solution to stop the reaction. Organic layers extracted from the obtained mixture with ethyl acetate are dried with sodium sulfate, and then concentrated with an evaporator to obtain 12.35 g of Compound 16-1.

Workup

  1. temperatureThe obtained solution is again cooled to −78° C.
  2. temperaturethe temperature of the solution is raised to room temperature over 120 minutes
  3. customthe reaction
  4. extractionOrganic layers extracted from the obtained mixture with ethyl acetate
  5. dry with materialare dried with sodium sulfate
  6. concentrationconcentrated with an evaporator

Sources & evidence

ORD record
ord-1475262ba7e045a3a7e2a397513bdafa
Source dataset
uspto-grants-2012_07
Patent number
US08211551B2

Reaction notes

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