Triphenylphosphine → 3-(Bromomethyl)-5-(trifluoromethyl)benzonitrile

HRID 391408

Reaktionsgleichung

Reaktionsgleichung von HRID 391408
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:6]#[N:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:34]N1C(=O)CCC1=O>C(Cl)Cl>[Br:34][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:6]#[N:7]

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 117012213-(Hydroxymethyl)-5-(trifluoromethyl)benzonitrile

Produkt 1

HCID 116013693-(Bromomethyl)-5-(trifluoromethyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-(Hydroxymethyl)-5-(trifluoromethyl)benzonitrile (0.33 mg, 1.64 mmol) and triphenylphosphine (0.86 g, 3.28 mmol) were combined in methylene chloride (6 mL) and cooled to 0° C. N-Bromosuccinimide (0.61 mg, 3.43 mmol) was introduced in portions and the reaction allowed to warm to room temperature. After 16 h, the reaction mixture was diluted with methylene chloride, washed with concentrated sodium bicarbonate (2×), brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (20% ethyl acetate/hexanes) gave 0.36 g (83%). 1H-NMR (CDCl3, 500 MHz) δ 7.97 (s, 2H), 7.84 (s, 1H), 4.50 (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 (20% ethyl acetate/hexanes) gave 0.36 g (83%)

Quellen und Nachweise

ORD-Eintrag
ord-7e23b24fbf744967ae3683bf41d8c9a8
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383821B2

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