HCID 12902850, compound → HCID 12902851, compound

HRID 1680700Notes

Reaction equation

HRID 1680700 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-dbd5c971c2e8417085e5cdbd39292c2a
Source dataset
uspto-grants-1981_06
Patent number
US04275221

Reaction notes

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