Triphenylphosphine → 3'-(Bromomethyl)-5'-(trifluoromethyl)biphenyl-4-carbonitrile

HRID 391371

Reaktionsgleichung

Reaktionsgleichung von HRID 391371
[Br:1]N1C(=O)CCC1=O.O[CH2:10][C:11]1[CH:12]=[C:13]([C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)[CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:1][CH2:10][C:11]1[CH:12]=[C:13]([C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)[CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 589936723'-(Hydroxymethyl)-5'-(trifluoromethyl)biphenyl-4-carbonitrile

Produkt 1

HCID 589934903'-(Bromomethyl)-5'-(trifluoromethyl)biphenyl-4-carbonitrileAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-bromosuccinimide (2.24 g, 12.6 mmol) was added to a 0° C. solution of 3′-(hydroxymethyl)-5′-(trifluoromethyl)biphenyl-4-carbonitrile (1.66 g, 6.0 mmol) and triphenylphosphine (3.14 g, 12.0 mmol) in THF (100 mL). The reaction was warmed to ambient temperature and stirred for 18 hours. The solvent was evaporated and the residue was purified by chromatography on SiO2 with a gradient of ethyl acetate/hexanes of 5% to 40%. The product 3′-(bromomethyl)-5′-(trifluoromethyl)biphenyl-4-carbonitrile (1.30 g, 64%) was obtained as a white solid. 1H-NMR (CDCl3, 400 MHz) δ 7.65-7.80 (m, 7H), 4.56 (s, 2H).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue was purified by chromatography on SiO2 with a gradient of ethyl acetate/hexanes of 5% to 40%

Quellen und Nachweise

ORD-Eintrag
ord-1b24b27c1ecc4ddebe9a66406204f0cb
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383821B2

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