Dibenzofuran → 2-Bromodibenzofuran

HRID 1893110Notes

Reaction equation

HRID 1893110 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.[Br:14]Br.O>C(O)(=O)C>[Br:14][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 568Dibenzofuran2×HCID 962WaterHCID 24408Bromine

Product 1

HCID 68562-BromodibenzofuranYield 31%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

150 g (892 mmol) of dibenzofuran and 1 L of acetic acid were loaded into a flask. Air in the flask was replaced with nitrogen, and dibenzofuran was dissolved in acetic acid under heat. 188 g (1.18 mol) of bromine were dropped to the solution while the solution was sometimes cooled with water. After that, the mixture was stirred for 20 hours while being cooled with air. The precipitated crystal was separated by filtration, washed with acetic acid and water in the stated order, and dried under reduced pressure. The resultant crystal was purified by distillation under reduced pressure. After that, the resultant was repeatedly recrystallized with methanol several times, whereby 66.8 g of 2-bromodibenzofuran were obtained (31% yield).

Workup

  1. temperatureunder heat
  2. temperaturewhile being cooled with air
  3. customThe precipitated crystal was separated by filtration
  4. washwashed with acetic acid and water in the stated order
  5. customdried under reduced pressure
  6. distillationThe resultant crystal was purified by distillation under reduced pressure
  7. customAfter that, the resultant was repeatedly recrystallized with methanol several times

Sources & evidence

ORD record
ord-625ea16c302c456fabd2a732f20fd8f1
Source dataset
uspto-grants-2013_08
Patent number
US08512875B2

Reaction notes

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