Sulfuric Acid → 4-Dimethylamino-phenylboric acid

HRID 963380

Reaktionsgleichung

Reaktionsgleichung von HRID 963380
Br[C:2]1[CH:10]=[CH:9][C:5]([N:6]([CH3:8])[CH3:7])=[CH:4][CH:3]=1.[Mg].C[O:13][B:14]([O:17]C)[O:15]C.S(=O)(=O)(O)O>O1CCCC1>[CH3:7][N:6]([CH3:8])[C:5]1[CH:9]=[CH:10][C:2]([O:13][B:14]([OH:17])[OH:15])=[CH:3][CH:4]=1

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 8470Trimethyl borateHCID 114654-bromo-N,N-dimethylanilineHCID 5462224Magnesium

Produkt 1

HCID 190817074-Dimethylamino-phenylboric acidAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of the corresponding Grignard compound is prepared from 16.8 g 4-bromo-N,N-dimethyl-aniline and 2.04 g of magnesium in 150 ml of tetrahydrofuran. This is now slowly added dropwise while stirring at -60° to a solution of 9.4 ml of trimethylborate in 50 ml of tetrahydrofuran under argon. Subsequently, the mixture is stirred at room temperature overnight. The mixture is poured on to ice-water, adjusted to pH 3-4 with dilute sulphuric acid and extracted with diethyl ether. The extract is dried, evaporated and the residue is recrystallized from water. 5.6 g (40%) of 4-dimethylamino-phenylboric acid are obtained. Mass spectrum: peaks inter alia at m/e: 164 (M±H, 100%).

Aufarbeitung

  1. additionThis is now slowly added dropwise
  2. extractionextracted with diethyl ether
  3. customThe extract is dried
  4. customevaporated
  5. customthe residue is recrystallized from water

Quellen und Nachweise

ORD-Eintrag
ord-45295211147146cc965004b4e34c1268
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05763450

Verknüpfte Notizen

Wird geladen…