Diisopropylethylamine → 1-Bromo-3-isocyanato-2-methyl-benzene

HRID 523274Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 523274
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[Br:13][C:14]1[C:15]([CH3:21])=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[Br:13][C:14]1[CH:20]=[CH:19][CH:18]=[C:16]([N:17]=[C:5]=[O:11])[C:15]=1[CH3:21]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 1235383-Bromo-o-toluidine

Produkt 1

HCID 655423311-Bromo-3-isocyanato-2-methyl-benzeneAusbeute 229 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A solution of triphosgene (2.25 g, 7.58 mmol) in toluene (27 mL), cooled in an ice-water bath, was treated slowly with a solution of 3-bromo-2-methylaniline (3.00 g, 16.1 mmol) and DIEA (5.6 mL, 32.2 mmol) in toluene (5.4 mL). The resulting suspension was stirred at room temperature for 2 h. The precipitate was removed by filtration and washed with EtOAc. The combined filtrates were diluted with EtOAc, washed with brine, dried and concentrated to provide 1-bromo-3-isocyanato-2-methylbenzene as a brown oil (3.68 g, 98% yield), used without purification. 1H NMR (400 MHz, DMSO-d6) δ 7.49 (dd, J=8.1, 0.9 Hz, 1H), 7.31 (dd, J=7.9, 0.7 Hz, 1H), 7.15 (td, J=8.0, 0.7 Hz, 1H), 2.38 (s, 3H).

Aufarbeitung

  1. customThe precipitate was removed by filtration
  2. washwashed with EtOAc
  3. additionThe combined filtrates were diluted with EtOAc
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-80aa8b1a961546129992fd756427e07d
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334290B2

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