Dibenzofuran → 2-Bromodibenzofuran

HRID 1844940Notes

Reaction equation

HRID 1844940 reaction equation
[Br:1]Br.[CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.O>C(O)(=O)C>[Br:1][C:4]1[CH:5]=[CH:6][C:7]2[O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[C:11]=2[CH:3]=1

Participants

5

Reactant 3

HCID 568DibenzofuranHCID 962WaterHCID 24408Bromine

Product 1

HCID 68562-BromodibenzofuranYield 13%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
50 °C

Procedure

Bromine (23.8 g, 0.156 mol) in acetic acid (5 g) is added at 50° C. to a solution of dibenzofuran (25 g, 0.149 mol) in acetic acid (230 g). The mixture is then stirred at 50° C. for 4 hours. The reaction mixture is cooled to room temperature and poured into H2O. The orange solid is washed with Na2S2O3 aq. and H2O. The crude product is then purified by recrystallization from toluene/CH2Cl2, wherein the pure product is obtained as a white solid (13% yield).

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. washThe orange solid is washed with Na2S2O3 aq. and H2O
  3. customThe crude product is then purified by recrystallization from toluene/CH2Cl2, wherein the pure product

Sources & evidence

ORD record
ord-d961893b784f46e3ad1000d738dd39ed
Source dataset
uspto-grants-2015_02
Patent number
US08946984B2

Reaction notes

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