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ChemicalBook CAS DataBase List 4-BROMO-1-METHYL-1H-INDOLE
590417-55-3

4-BROMO-1-METHYL-1H-INDOLE synthesis

7synthesis methods
-

Yield: 91%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 140;

Steps:

4.2.10 4-Bromo-3-acetyl-1-methyl-1H-indole (32)
A suspension of 31 (8.8g, 45mmol), potassium carbonate (4.5g, 32mmol), and dimethyl carbonate (12g, 0.13mol) in DMF (56mL) was gradually heated to 140°C over 30min and stirred for 3.5h. After cooling to room temperature, the insoluble solids were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was distilled under reduced pressure (0.2mmHg, 155-180°C) to give 8.5g (91%) of 4-bromo-1-methylindole as a yellow liquid. Its 1H NMR spectroscopic data were consistent with those reported in the literature.48

References:

Fu, Tsung-Hao;McElroy, William T.;Shamszad, Mariam;Heidebrecht Jr., Richard W.;Gulledge, Brian;Martin, Stephen F. [Tetrahedron,2013,vol. 69,# 27-28,p. 5588 - 5603]

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