Water → 1-Bromo-4-(isocyanomethyl)-2-methylbenzene

HRID 1844632Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1844632
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][NH:7][CH:8]=O)=[CH:4][C:3]=1[CH3:12].P(Cl)(Cl)(Cl)=O.O.C(=O)([O-])O.[Na+]>ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][N+:7]#[C-:8])=[CH:4][C:3]=1[CH3:12]

Komponenten

7

Edukt 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 58497978N-(4-bromo-3-methyl-benzyl)-formamide

Produkt 1

HCID 584979501-Bromo-4-(isocyanomethyl)-2-methylbenzeneAusbeute 114,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of N-(4-bromo-3-methyl-benzyl)-formamide (4.3 g) (Example I2) in dichloromethane (70 ml) was added a solution of phosphorus oxychloride (2.8 g) in dichloromethane (15 ml) at 0-5° C. The reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was poured onto a mixture of ice and water (400 ml), and sodium hydrogen carbonate (saturated) (100 ml) and ethyl acetate (250 ml) were added. The phases were separated and the organic phase was washed with brine, dried over sodium sulfate and concentrated to give 1-bromo-4-isocyanomethyl-2-methyl-benzene (4.52 g) as a in brown oil. 1H-NMR (400 MHz, CDCl3): 7.54 (m, 1H), 7.22 (s, 1H), 7.03 (m, 1H), 4.57 (s, 2H), 2.42 (s, 3H) ppm.

Aufarbeitung

  1. customat 0-5° C
  2. additionwere added
  3. customThe phases were separated
  4. washthe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-41f15bcfd21941ad90bcf965facb3905
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946447B2

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