Bromine → 3-(8-Bromo-4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-5-fluorobenzonitrile

HRID 1258101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1258101
[CH3:1][C:2]1([CH3:22])[C:7]2[CH:8]=[C:9]([C:12]3[CH:13]=[C:14]([CH:17]=[C:18]([F:20])[CH:19]=3)[C:15]#[N:16])[CH:10]=[CH:11][C:6]=2[NH:5][C:4](=[O:21])[O:3]1.C([O-])(=O)C.[Na+].[Br:28]Br>C(O)(=O)C>[Br:28][C:11]1[C:6]2[NH:5][C:4](=[O:21])[O:3][C:2]([CH3:22])([CH3:1])[C:7]=2[CH:8]=[C:9]([C:12]2[CH:13]=[C:14]([CH:17]=[C:18]([F:20])[CH:19]=2)[C:15]#[N:16])[CH:10]=1

Komponenten

5

Edukt 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 98391343-(4,4-dimethyl-2-oxo-2,4-dihydro-1H-benzo[d][1,3]oxazin-6-yl)-5-fluorobenzonitrile

Produkt 1

HCID 220219003-(8-Bromo-4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-5-fluorobenzonitrileAusbeute 75,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a mixture of 3-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-5-fluorobenzonitrile (0.5 g, 1.7 mmol) and sodium acetate (0.2 g, 2.4 mmol) in acetic acid (5 mL) was added, at room temperature under nitrogen, bromine (0.12 mL, 2.34 mmol). The reaction mixture was stirred for 20 hours and then poured into ice water (30 mL). The precipitate was collected on a filter and washed with water (3×5 mL) to yield 3-(8-bromo-4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-5-fluorobenzonitrile as an off-white solid (0.48 g, 75%): mp 216-217° C.; 1H-NMR (DMSO-d6) δ 9.78 (s, 1H), 8.18 (t, 1H, J=1.6 Hz), 8.02-8.08 (m, 2H), 7.81 (m, 1H), 7.75 (d, 1H, J=1.8 Hz), 1.66 (s, 6H). MS (ESI) m/z 373, 375 [M−H]−.

Aufarbeitung

  1. additionwas added, at room temperature under nitrogen
  2. customThe precipitate was collected on
  3. filtrationa filter
  4. washwashed with water (3×5 mL)

Quellen und Nachweise

ORD-Eintrag
ord-96717d76d8e74183aa7befcde98af9df
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466146B2

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