Phenylboronic Acid → (1,1'-Biphenyl)-2-methanol

HRID 227870

Reaktionsgleichung

Reaktionsgleichung von HRID 227870
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].[K+].Br[C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][OH:16]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>[OH:16][CH2:15][C:14]1[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 3

HCID 66827Phenylboronic AcidHCID 728502-Bromobenzyl alcoholHCID 522689Potassium Fluoride

Produkt 1

HCID 76229(1,1'-Biphenyl)-2-methanolAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 27342152-(Di-tert-butylphosphino)biphenylKatalysator

Versuchsvorschrift

An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol %), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol %), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 2-bromobenzyl alcohol (187 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 153 mg (83%) of the title compound.

Aufarbeitung

  1. customAn oven dried resealable Schlenk tube
  2. customwas evacuated
  3. customThe tube was evacuated
  4. additionwas added through a rubber septum
  5. customThe tube was sealed with a teflon screwcap
  6. customhad been completely consumed
  7. additionThe reaction mixture was then diluted with ether (30 mL)
  8. filtrationfiltered through celite
  9. concentrationconcentrated
  10. customThe crude material was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-35f3a7b6348c406bb2fb1c63e01b493c
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560582B2

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