Acetic Acid → 2-Bromodibenzofuran

HRID 2283155Notes

Reaction equation

HRID 2283155 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.[Br:18]Br>O>[Br:18][C:2]1[CH:3]=[CH:4][C:5]2[O:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[C:9]=2[CH:1]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 568DibenzofuranHCID 24408Bromine

Product 1

HCID 68562-BromodibenzofuranYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

150 grams (892 mmol) of dibenzofuran and 1 L of acetic acid were added into a flask. The air in the flask was replaced with nitrogen, and then the contents were dissolved under heating. 188 grams (1.18 mol) of bromine were dropped to the solution while the flask was sometimes cooled with water. After that, the mixture was stirred for 20 hours under air cooling. The precipitated crystal was separated by filtration, and was then sequentially washed with acetic acid and water. The washed crystal was dried under reduced pressure. The resultant crystal was purified by distillation under reduced pressure, and was then repeatedly recrystallized with methanol several times. Thus, 66.8 g of 2-bromodibenzofuran were obtained (in 31% yield). The resultant was identified as Intermediate 5 by FD-MS analysis.

Workup

  1. dissolutionthe contents were dissolved
  2. temperatureunder heating
  3. temperaturecooling
  4. customThe precipitated crystal was separated by filtration
  5. washwas then sequentially washed with acetic acid and water
  6. customThe washed crystal was dried under reduced pressure
  7. distillationThe resultant crystal was purified by distillation under reduced pressure
  8. customwas then repeatedly recrystallized with methanol several times

Sources & evidence

ORD record
ord-886e364c2cdf481e95bbd0572b310034
Source dataset
uspto-grants-2015_09
Patent number
US09145363B2

Reaction notes

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