Phosphorus tribromide → (3-Bromoprop-1-yn-1-yl)benzene

HRID 481571

Reaktionsgleichung

Reaktionsgleichung von HRID 481571
P(Br)(Br)[Br:2].[C:5]1([C:11]#[C:12][CH2:13]O)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(OCC)C.N1C=CC=CC=1>[C:5]1([C:11]#[C:12][CH2:13][Br:2])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Komponenten

5

Edukt 2

HCID 24614Phosphorus tribromideHCID 1231153-Phenyl-2-propyn-1-ol

Produkt 1

HCID 10987157(3-Bromoprop-1-yn-1-yl)benzeneAusbeute 248,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineKatalysatorHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Phosphorous tribromide (2.62 mL, 27.6 mmol) was added to a solution of 3-phenyl-2-propyn-1-ol (10.0 g, 76 mmol) and pyridine (0.14 mL, 1.77 mmol) in diethyl ether (22 mL) at a rate to maintain reflux. After addition, the mixture was heated at 40° C. for 2 h. The mixture was cooled and poured onto ice. The organic layer was separated and diluted with diethyl ether (100 mL), washed with saturated sodium bicarbonate (2×50 mL) and saturated sodium chloride (50 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to afford 1-phenyl-3-bromo-1-propyne (13.4 g, 90%). ##STR184## Step 2(E)--Preparation of 2-(benzyloxy)bromoethane

Aufarbeitung

  1. temperatureto maintain
  2. temperaturereflux
  3. additionAfter addition
  4. temperatureThe mixture was cooled
  5. additionpoured onto ice
  6. customThe organic layer was separated
  7. additiondiluted with diethyl ether (100 mL)
  8. washwashed with saturated sodium bicarbonate (2×50 mL) and saturated sodium chloride (50 mL)
  9. dry with materialThe organic layer was dried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d77a592b0453471e91bfda7c4f1e1151
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05789434

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