Diethyl Ether → 1,3-dibromo-dibenzofuran

HRID 654639Notes

Reaction equation

HRID 654639 reaction equation
C(ON=O)(C)(C)C.N[C:9]1[C:21]([Br:22])=[CH:20][C:12]2[O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:11]=2[C:10]=1[Br:23].CCOCC>CN(C=O)C>[Br:23][C:10]1[C:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[O:13][C:12]=2[CH:20]=[C:21]([Br:22])[CH:9]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 10906Tert-Butyl nitriteHCID 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-butylnitrite (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-5e8e6bc24bba4ec0b15bdcda33695775
Source dataset
uspto-grants-1992_07
Patent number
US05132420

Reaction notes

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