HCID 12902850, compound → HCID 12902851, compound

HRID 128085Notes

Reaction equation

HRID 128085 reaction equation
[Br:1][C:2]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:15]=[CH:14][C:3]=1[O:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=O>O>[Br:1][C:2]1[C:3]2[O:4][CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]=2[CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:17]=1

Participants

3

Reactant 1

HCID 12902850HCID 12902850, compound

Product 1

HCID 12902851HCID 12902851, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 156 g. of the product of step A and 1 kg. of polyphosphoric acid is heated at 100° C. for seven days. The reaction mixture is poured into 5 liters of water and stirred, then extracted with 2 liters of chloroform. The dried extracts are treated with decolorizing charcoal, then evaporated. The residue is chromatographed on silica gel, eluting with carbon tetrachloride. The residue is triturated with hexane to provide 7-bromo-3,5-diphenylbenzofuran as a pale yellow solid. The structural assignment is supported by infrared and nuclear magnetic resonance spectral analysis.

Workup

  1. additionA mixture of 156 g
  2. extractionextracted with 2 liters of chloroform
  3. additionThe dried extracts are treated with decolorizing charcoal
  4. customevaporated
  5. customThe residue is chromatographed on silica gel
  6. washeluting with carbon tetrachloride
  7. customThe residue is triturated with hexane

Sources & evidence

ORD record
ord-04dad6cb6acf471490ce2c2081d16e8a
Source dataset
uspto-grants-1981_03
Patent number
US04258213

Reaction notes

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