Hydrochloric Acid → B-(4-Nonylphenyl)boronic acid

HRID 395244Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 395244
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5][CH:4]=1.[B:18](OC)([O:21]C)[O:19]C.Cl.[Cl-].[Na+]>O1CCCC1>[CH2:9]([C:6]1[CH:7]=[CH:8][C:3]([B:18]([OH:21])[OH:19])=[CH:4][CH:5]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 8470Trimethyl borateHCID 5462224MagnesiumHCID 126030951-Bromo-4-nonylbenzene

Produkt 1

HCID 4589192B-(4-Nonylphenyl)boronic acidAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of the Grignard compound prepared from 0.55 mol of magnesium and 0.37 mol of 1 -bromo-4-nonylbenzene in 550 ml of dry tetrahydrofuran is added dropwise to a solution of 0.4 mol of trimethyl borate in 400 ml of dry tetrahydrofuran at 0° C. under a protective gas atmosphere. The mixture is stirred for an additional 2.5 h at this temperature. Then 600 ml of 10% stength hydrochloric acid are added and the resulting mixture is stirred at room temperature for 30 min. After addition of 120 g of sodium chloride, the reaction mixture is extracted with tert-butyl methyl ether, the combined organic extracts are washed with saturated sodium chloride solution and dried with magnesium sulfate. The solvent is removed under reduced pressure and the raw product is recrystallized from acetonitrile, giving 72 g (79%) of 4-nonylphenylboronic acid.

Aufarbeitung

  1. stirringthe resulting mixture is stirred at room temperature for 30 min
  2. extractionthe reaction mixture is extracted with tert-butyl methyl ether
  3. washthe combined organic extracts are washed with saturated sodium chloride solution
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe raw product is recrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-4c53473a7d4441e69c036af7060e23f2
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06605323B1

Notizen zur Reaktion

Wird geladen…