Hydrochloric Acid → [4-[Bis(4-methylphenyl)amino]phenyl]boronic acid

HRID 1755522Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1755522
Br[C:2]1[CH:22]=[CH:21][C:5]([N:6]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[Li]CCCC.[B:28](OC)([O:31]C)[O:29]C.Cl>C1COCC1>[C:10]1([CH3:13])[CH:11]=[CH:12][C:7]([N:6]([C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)[C:5]2[CH:4]=[CH:3][C:2]([B:28]([OH:31])[OH:29])=[CH:22][CH:21]=2)=[CH:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 111427014-Bromo-4',4''-dimethyltriphenylamine2×HCID 178418339Butyllithium

Produkt 1

HCID 23083792[4-[Bis(4-methylphenyl)amino]phenyl]boronic acidAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 4-bromo-N,N-di-p-tolylaniline (Compound 25) (12.55 g, 35.6 mmol) in anhydrous THF (100 mL), was added n-BuLi solution (16 mL, 2.5 M in hexanes) at −78° C. slowly. The resulting solution was stirred at −78° C. for about one hour. Then a freshly distilled trimethyl borate (B(OCH3)3) (5.6 mL) was added. The solution turned to yellow immediately, and was stirred at RT for about 2 hours. After addition of 1N HCl solution (150 mL), the whole was stirred at RT for about 18 hours and concentrated. The resulting solid was filtered and washed with diethyl ether to give a light yellow solid (Compound 26) (5.8 g, in 56% yield).

Aufarbeitung

  1. stirringwas stirred at RT for about 2 hours
  2. stirringthe whole was stirred at RT for about 18 hours
  3. concentrationconcentrated
  4. filtrationThe resulting solid was filtered
  5. washwashed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e8d9a463afab493ba04c46f319dad949
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09172051B2

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