Water → 2-(2,4,6-Trimethoxybenzylthio)phenylboronic acid

HRID 1987475

Reaktionsgleichung

Reaktionsgleichung von HRID 1987475
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:9][C:10]1[C:15]([O:16][CH3:17])=[CH:14][C:13]([O:18][CH3:19])=[CH:12][C:11]=1[O:20][CH3:21].[Li]CCCC.[B:27](OC)([O:30]C)[O:28]C.O>C1COCC1>[CH3:21][O:20][C:11]1[CH:12]=[C:13]([O:18][CH3:19])[CH:14]=[C:15]([O:16][CH3:17])[C:10]=1[CH2:9][S:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[B:27]([OH:30])[OH:28]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8470Trimethyl borateHCID 66870845(2-Bromophenyl)(2,4,6-trimethoxybenzyl)sulfaneHCID 178418339Butyllithium

Produkt 1

HCID 686436172-(2,4,6-Trimethoxybenzylthio)phenylboronic acidAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 4.22 g (2-bromophenyl)(2,4,6-trimethoxybenzyl)sulfane (11.56 mmol) in 150 ml dry THF at −78° C. was added slowly 5.6 ml 2.5M n-BuLi. The solution was stirred at −78° C. for 25 minutes. 1.6 ml B(OMe)3 was added at −78° C. The reaction was stirred 2 hours at RT. 100 ml water was added, stirred overnight. The mixture was extracted with ethyl acetate (2×100 ml). The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by gradient chromatography (hexane:ethyl acetate 60:40) yielded 1.762 g product (5.3 mmol, 46% yield).

Aufarbeitung

  1. stirringThe reaction was stirred 2 hours at RT
  2. stirringstirred overnight
  3. extractionThe mixture was extracted with ethyl acetate (2×100 ml)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by gradient chromatography (hexane:ethyl acetate 60:40)

Quellen und Nachweise

ORD-Eintrag
ord-5bb9f67d1d0041ea82ea67177f16ec95
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07550505B2

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