Bromine → 2-Bromo-1-[8-(tert-butyl)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-1-ethanone

HRID 657935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 657935
[C:1]([C:5]1[C:14]2[O:13][CH2:12][CH2:11][N:10]([CH3:15])[C:9]=2[CH:8]=[C:7]([C:16](=[O:18])[CH3:17])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br:19]Br>C(O)(=O)C.C1(C)C=CC=CC=1>[Br:19][CH2:17][C:16]([C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:14]2[O:13][CH2:12][CH2:11][N:10]([CH3:15])[C:9]=2[CH:8]=1)=[O:18]

Komponenten

5

Edukt 2

HCID 24408BromineHCID 589100321-[8-(tert-Butyl)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-1-ethanone

Produkt 1

HCID 589099482-Bromo-1-[8-(tert-butyl)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-1-ethanoneAusbeute 19,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

1-(8-tert-Butyl-4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)ethanone (250 mg, purchased from Chembiotek, India) was heated to from 50° C. to 55° C. in a mixture of acetic acid (4 ml) and toluene (8 ml). At this temperature, bromine (200 mg dissolved in acetic acid) was cautiously added dropwise. After 2.5 h, the heating was removed, and the mixture was admixed at RT with ice-water and extracted three times with toluene. The combined organic phases were dried over sodium sulfate, filtered and concentrated. The crude product was purified using silica gel, so as to obtain 65 mg of the desired compound, as well as a further 43 mg of product which was slightly contaminated and 37 mg of reactant.

Aufarbeitung

  1. customthe heating was removed
  2. customwas admixed at RT with ice-water
  3. extractionextracted three times with toluene
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified

Quellen und Nachweise

ORD-Eintrag
ord-81d5a1babcb34a0d9788f4110b4ac30a
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076336B2

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