Diethyl Ether → 1,3-dibromo-dibenzofuran

HRID 1494275Notes

Reaction equation

HRID 1494275 reaction equation
N[C:2]1[C:14]([Br:15])=[CH:13][C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[C:3]=1[Br:16].CCOCC>CN(C=O)C>[Br:16][C:3]1[C:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[O:6][C:5]=2[CH:13]=[C:14]([Br:15])[CH:2]=1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 19737928HCID 19737928, compound

Product 1

HCID 5262881,3-dibromo-dibenzofuranYield 116.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of t-butylnitride (0.89 ml, 7.2 mmol) dissolved in 10 ml of DMF at 50° C. was added dropwise a solution of 2-amino-1,3-dibromodibenzofuran 17 (1.0 g, 2.9 mmol) in 10 ml of DMF with nitrogen evolution. After stirring at 50° C. for 1 hour the reaction was diluted into ether and washed successively with H2O and saturated NaCl. Drying over MgSO4 and evaporation gave 1.1 g of a red solid which was purified by flash chromatography through 100 g of silica gel (20% methylene chloride:hexane) yielding 650 mg (68%) of the title compound as a pale orange solid.

Workup

  1. washwashed successively with H2O and saturated NaCl
  2. dry with materialDrying over MgSO4 and evaporation

Sources & evidence

ORD record
ord-281733f8fe2646f295dc20a0b23d5156
Source dataset
uspto-grants-1991_06
Patent number
US05025008

Reaction notes

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