4-Bromobiphenyl → HCID 20291240, compound

HRID 1413953Notes

Reaction equation

HRID 1413953 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[Mg].C(Br)CBr.[C:19]([C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[NH4+]>O1CCCC1>[C:4]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:5]=[CH:6][CH:1]=[CH:2][C:3]=1[C:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1)[OH:26]

Participants

7

Reactant 5

HCID 71014-BromobiphenylHCID 78391,2-DibromoethaneHCID 25517Ammonium ChlorideHCID 267314-BenzoylpyridineHCID 5462224Magnesium

Product 1

HCID 20291240HCID 20291240, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
25 °C

Procedure

A solution of 111.0 g (0.50 mole) of 4-biphenyl bromide in 200 ml of dry tetrahydrofuran (THF) was added slowly to a mixture of 12.10 g (0.5 gram-atom) of magnesium, 2 ml of ethylenedibromide and 200 ml of THF at such a rate as to maintain reflux. After addition the mixture was refluxed for 0.5 hours, cooled and treated over 0.5 hours with a solution of 82.3 g (0.45 mole) of 4-benzoylpyridine in 600 ml THF. The resulting slurry was stirred 0.5 hours at 25° C. and treated with 1000 ml 20% ammonium chloride solution. The organic layer was separated, filtered, the filtrate dried, filtered and stripped. The residue was triturated with ether and filtered. This solid was recrystallized from ethanol, chloroform, and finally toluene to give α-(1,4'-biphenyl)-yl-α-phenyl-4-pyridinemethanol as a white solid, m.p. after drying in vacuo at 70° C.; 173.5°-175.5° C.

Workup

  1. temperatureto maintain
  2. temperaturereflux
  3. additionAfter addition the mixture
  4. temperaturewas refluxed for 0.5 hours
  5. temperaturecooled
  6. customThe organic layer was separated
  7. filtrationfiltered
  8. customthe filtrate dried
  9. filtrationfiltered
  10. customThe residue was triturated with ether
  11. filtrationfiltered
  12. customThis solid was recrystallized from ethanol, chloroform, and finally toluene

Sources & evidence

ORD record
ord-c02db72ba55f452c83a050332f318c0b
Source dataset
uspto-grants-1981_02
Patent number
US04251655

Reaction notes

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