Triphenylphosphine → 1-Bromo-3-(bromomethyl)-5-nitrobenzene

HRID 391451

Reaktionsgleichung

Reaktionsgleichung von HRID 391451
[Br:1][C:2]1[CH:3]=[C:4]([CH2:11]O)[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:32]N1C(=O)CCC1=O>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH2:11][Br:32])[CH:3]=1

Komponenten

6

Edukt 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 14866972(3-Bromo-5-nitrophenyl)methanol

Produkt 1

HCID 148669731-Bromo-3-(bromomethyl)-5-nitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(3-Bromo-5-nitrophenyl)methanol (2.0 g, 8.65 mmol) and triphenylphosphine (4.5 g, 17.3 mmol) were combined in tetrahydrofuran (40 mL) and cooled to 0° C. N-Bromosuccinimide (3.2 g, 18.2 mmol) was introduced in portions and the reaction allowed to warm to room temperature. After 16 h, the reaction mixture was diluted with ethyl acetate, washed with concentrated sodium bicarbonate (2×), brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (5% ethyl acetate/hexanes) gave 2.2 g (84%) as a white powder. 1H-NMR (CDCl3, 300 MHz) 8.27 (s, 1H), 8.16 (s, 1H), 7.84 (s, 1H), 4.45 (s, 2H).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. washwashed with concentrated sodium bicarbonate (2×), brine (2×)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customColumn chromatography on silica gel (5% ethyl acetate/hexanes) gave 2.2 g (84%) as a white powder

Quellen und Nachweise

ORD-Eintrag
ord-036a52c95d9b42dea2d4a95452bfd532
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383821B2

Verknüpfte Notizen

Wird geladen…