Phosphorus tribromide → 2-(Bromomethyl)-1,2,3,4-tetrahydronaphthalene

HRID 849996

Reaktionsgleichung

Reaktionsgleichung von HRID 849996
O[CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.P(Br)(Br)[Br:14]>C(Cl)Cl>[Br:14][CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1

Komponenten

4

Edukt 2

HCID 24614Phosphorus tribromideHCID 245056(1,2,3,4-Tetrahydronaphthalen-2-yl)methanol

Produkt 1

HCID 127232822-(Bromomethyl)-1,2,3,4-tetrahydronaphthaleneAusbeute 124,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2-hydroxymethyl-1,2,3,4-tetrahydronaphthalene (2.28 g, 14.0 mmol) in 100 ml of CH2Cl2 was treated with PBr3 (1.28 g, 4.73 mmol) at 0° C. The mixture was stirred at room temperature for 72 hours then poured onto 100 g of ice. The organic layer was isolated, washed with 10% K2CO4 aqueous solution, H2O , sat'd brine, and then dried over Na2SO4. After filtration and removal of solvent, the residue was purified by chromatography (SiO2, EtOAc:hexane, 1:10) to give a colorless oil (1.33 g, 41.6%); 1H NMR (CDCl3, 300 MHz) δ 1.55 (m, 1H), 2.11 (m, 1H), 2.11 (m, 2H), 2.58 (dd, J1 =16.2 Hz, J2 =10.2 Hz, 1H), 2.80-3.10 (m, 3H), 3.45 (d, J=6.3 Hz, 2H), 7.10 (m, 4H).

Aufarbeitung

  1. customThe organic layer was isolated
  2. washwashed with 10% K2CO4 aqueous solution, H2O
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and removal of solvent
  5. customthe residue was purified by chromatography (SiO2, EtOAc:hexane, 1:10)

Quellen und Nachweise

ORD-Eintrag
ord-a9d32f7ff2574583aeee051194433979
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06015819

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