Pyridine → 2-bromo-2,3-dihydro-1H-indene

HRID 265227

Reaktionsgleichung

Reaktionsgleichung von HRID 265227
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1O.N1C=CC=CC=1.P(Br)(Br)[Br:18]>C(Cl)(Cl)Cl>[Br:18][CH:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 779362-Indanol

Produkt 1

HCID 109654632-bromo-2,3-dihydro-1H-indeneAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To 2-indanol (Aldrich) (105 g, 0.78 mol) in pyridine (16 mL, 0.2 mol) and 340 mL of chloroform at -15 C. was added PBr3 (84 mL, 0.89 mol) over 45 min. The reaction mixture was stirred overnight at room temperature and extracted by addition of 450 mL of chloroform and 500 g of ice. The organic layer was washed twice with water, and dried over Na2SO4. The solvent was evaporated in vacuo, leaving a brown semi-solid. The product was distilled rapidly in vacuo and then fractionated to give 69 g (45%) 2-bromoindane, bp 90-93 /3 mmHg; nd23 =1.5837.

Aufarbeitung

  1. extractionextracted by addition of 450 mL of chloroform and 500 g of ice
  2. washThe organic layer was washed twice with water
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated in vacuo
  5. customleaving a brown semi-solid
  6. distillationThe product was distilled rapidly in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-debf2fa9dc904d69b847e44380d136c6
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648336

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