Triphenylphosphine → Ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenyl(2,4-dimethoxybenzyl)carbamate

HRID 495659

Reaktionsgleichung

Reaktionsgleichung von HRID 495659
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([NH:12][C:13](=[O:17])[O:14][CH2:15][CH3:16])=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1.[CH3:21][O:22][C:23]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:24]=1[CH2:25]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:9])[F:11])[C:5]([N:12]([CH2:25][C:24]2[CH:27]=[CH:28][C:29]([O:31][CH3:32])=[CH:30][C:23]=2[O:22][CH3:21])[C:13](=[O:17])[O:14][CH2:15][CH3:16])=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 817502,4-Dimethoxybenzyl alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 20827743Ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenylcarbamate

Produkt 1

HCID 22327366Ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenyl(2,4-dimethoxybenzyl)carbamateAusbeute 53,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenylcarbamate (1049.3 mg), 2,4-dimethoxybenzyl alcohol (1.7217 g) and triphenylphosphine (3.0183 g) in tetrahydrofuran (15 ml) was added diethyl azodicarboxylate (2.2505 g). The mixture was stirred at room temperature for 8 hours, and then concentrated in vacuo. The resultant residue was purified by silica gel column (110 g, hexane:ethyl acetate=20:1→10:1) to give the title compound (796.8 mg, 53%) and recovered ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenylcarbamate (489.2 mg, 47%).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customThe resultant residue was purified by silica gel column (110 g, hexane:ethyl acetate=20:1→10:1)

Quellen und Nachweise

ORD-Eintrag
ord-e54fe271e5a34b3ca8a44a208e704701
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06939887B2

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