Bromine → 5-Bromoindoline

HRID 355093

Reaktionsgleichung

Reaktionsgleichung von HRID 355093
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=O)C.[Br:13]Br>C(O)(=O)C>[Br:13][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[NH:4][CH2:5][CH2:6]2

Komponenten

4

Edukt 2

HCID 24408BromineHCID 276731-(2,3-Dihydro-1H-indol-1-yl)ethan-1-one

Produkt 1

HCID 34115665-BromoindolineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Gall et al. [J. Org. Chem., Vol. 20 (1955), p. 1538] describes the direct bromination of 1-acetyl-indoline in glacial acetic acid with bromine followed by saponification to obtain 5-bromo-indoline in 85% yield but attempts to repeat the process with chlorine results in only about a 45% yield of 5-chloro-1-acetyl-indoline. The latter result is not surprising in view of references such as Thesing et al. [Chem. Ber., Vol. 95 (1962), p. 2205], German Pat. No. 1,123,668, British Pat. No. 919,864 and the Chemistry of Heterocyclic Compounds, Vol. 25, Indoles, part II, Wiley Interscience, New York, London, Sidney, Toronto, 1972 p. 129 which teach that the reaction of N-acetylated-indoline-2-sulfonates in glacical acetic acid with chlorine, hypochlorous acid or alkali metal hypochlorites results in a variety of chlorinated products including 5- and 7-chloro compounds. Japanese Patent Application Ser. No. P 69-27967 (1969) teaches that these difficulties may be avoided by reacting 1-acetyl-indoline with N-chlorosuccinimide in carbon tetrachloride.

Quellen und Nachweise

ORD-Eintrag
ord-48cef17359854ab18669cb541b5843e6
Quelldatensatz
uspto-grants-1983_03
Patentnummer
US04377699

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