Carbon tetrabromide → 1,3-Dioxane, 5-(2-bromoethyl)-2,2-dimethyl-

HRID 908526

Reaktionsgleichung

Reaktionsgleichung von HRID 908526
[CH3:1][C:2]1([CH3:11])[O:7][CH2:6][CH:5]([CH2:8][CH2:9]O)[CH2:4][O:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:32].C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:32][CH2:9][CH2:8][CH:5]1[CH2:6][O:7][C:2]([CH3:11])([CH3:1])[O:3][CH2:4]1

Komponenten

6

Edukt 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 118160112-(2,2-Dimethyl-1,3-dioxan-5-yl)ethanol

Produkt 1

HCID 1789881,3-Dioxane, 5-(2-bromoethyl)-2,2-dimethyl-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of compound 32 (84 g, 0.528 mol) in dry DMF (500 mL) was added triphenylphosphine (207 g, 0.79 mol) with vigorous stirring until it becomes a clear solution. The mixture was cooled to 0° C. and added CBr4 (260 g, 0.79 mol) portion wise over a period of 30 min and allowed to stir at RT for 5 h. The reaction mixture was cooled to 0° C., added saturated NaHCO3 solution (200 mL) and extracted with hexane (4×200 mL). The combined organic layer was dried, concentrated under vacuum and the crude title compound (117 g) was used for next reaction without any purification. TLC: Pet. ether/EtOAc, 7:3, Rf=0.6

Aufarbeitung

  1. stirringto stir at RT for 5 h
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. extractionextracted with hexane (4×200 mL)
  4. customThe combined organic layer was dried
  5. concentrationconcentrated under vacuum
  6. customthe crude title compound (117 g) was used for next reaction without any purification

Quellen und Nachweise

ORD-Eintrag
ord-8a9400e2ee204391b432642c46834d37
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017620B2

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