Phosphorus tribromide → 6-(1-Bromoethyl)-4,4-dimethylchroman

HRID 2118519

Reaktionsgleichung

Reaktionsgleichung von HRID 2118519
[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12](O)[CH3:13])[CH:10]=2)[O:5][CH2:4][CH2:3]1.P(Br)(Br)[Br:17]>CCOCC.N1C=CC=CC=1.CCCCCC>[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([Br:17])[CH3:13])[CH:10]=2)[O:5][CH2:4][CH2:3]1

Komponenten

6

Edukt 2

HCID 24614Phosphorus tribromideHCID 140102484,4-Dimethyl-6-(1-hydroxyethyl)chroman

Produkt 1

HCID 140102506-(1-Bromoethyl)-4,4-dimethylchromanAusbeute 83,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049PyridineKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 8058HexaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

6.2 g of 4,4-dimethyl-6-(1-hydroxyethyl)chromane were dissolved in 3 ml of absolute ether and 20 ml of hexane and the solution was treated with 3 drops of pyridine. At a temperature of 0°-5° C. there was slowly added dropwise thereto a solution of 5.4 g of phosphorus tribromide in 20 ml of hexane. The mixture was stirred at 0° C. for a further 3 hours, poured onto ice and extracted with ether. The organic phase was washed with dilute sodium bicarbonate solution and water, dried over sodium sulphate and evaporated. There were obtained 4.5 g of 4,4-dimethyl-6-(1-bromoethyl)chromane in the form of a reddish oil which was converted into the phosphonium bromide without further purification.

Aufarbeitung

  1. additionAt a temperature of 0°-5° C. there was slowly added dropwise
  2. additionpoured onto ice
  3. extractionextracted with ether
  4. washThe organic phase was washed with dilute sodium bicarbonate solution and water
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-b1566a18aafd4e60b56d5a61e499e417
Quelldatensatz
uspto-grants-1987_07
Patentnummer
US04678793

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