Bromobenzene → alpha-Phenyl[1,1'-biphenyl]-4-methanol

HRID 2305261

Reaktionsgleichung

Reaktionsgleichung von HRID 2305261
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[C:9]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][CH:10]=1.[NH4+].[Cl-]>C1COCC1>[C:2]1([CH:15]([C:12]2[CH:13]=[CH:14][C:9]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:10][CH:11]=2)[OH:16])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 7961BromobenzeneHCID 25517Ammonium ChlorideHCID 76689(1,1'-Biphenyl)-4-carboxaldehydeHCID 5462224Magnesium

Produkt 1

HCID 95512alpha-Phenyl[1,1'-biphenyl]-4-methanolAusbeute 39,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

A mixture of bromobenzene (0.3 mol) in THF (300 ml) was added dropwise to a mixture of magnesium (0.32 mol) in THF (20 ml). The mixture was stirred and refluxed for 1 hour. A mixture of 4-biphenylcarboxaldehyde (0.3 mol) in THF (500 ml) was added dropwise. The mixture was stirred and refluxed for 2 hours, at room temperature overnight, poured out into a saturated NH4Cl solution and extracted with DCM. The organic layer was separated, washed three times, dried, filtered and the solvent was evaporated. The residue was triturated in hexane, filtered off and purified over silica gel on a glass filter (eluent: CH2Cl2 100%). The pure fractions were collected and the solvent was evaporated. The residue was triturated in DIPE, filtered off and dried, yielding 31 g of (±)-α-phenyl(1,1′-biphenyl)-4-methanol (interm. 23).

Aufarbeitung

  1. temperaturerefluxed for 1 hour
  2. additionwas added dropwise
  3. stirringThe mixture was stirred
  4. extractionextracted with DCM
  5. customThe organic layer was separated
  6. washwashed three times
  7. customdried
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customThe residue was triturated in hexane
  11. filtrationfiltered off
  12. custompurified over silica gel on a glass
  13. filtrationfilter (eluent: CH2Cl2 100%)
  14. customThe pure fractions were collected
  15. customthe solvent was evaporated
  16. customThe residue was triturated in DIPE
  17. filtrationfiltered off
  18. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e60be3078c484e729af67d107b00b8f3
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06440440B1

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