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ChemicalBook CAS DataBase List (5-BROMO-1H-INDOL-2-YL)METHANOL

(5-BROMO-1H-INDOL-2-YL)METHANOL synthesis

3synthesis methods
16732-70-0 Synthesis
Ethyl 5-Bromoindole-2-carboxylate

16732-70-0
280 suppliers
$6.00/1g

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Yield:53590-48-0 97%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 0 - 20; for 2 h;Inert atmosphere;

Steps:

1.1 Step-1: Preparation of (5-bromo-lH-indol-2-yl)methanol (2)

To a solution of ethyl 5-bromo-lH-indole-2-carboxylate (1, 5.0 g, 18.6 mmol) in THF (35 mL) was added solution of 1 M lithium aluminum hydride in THF (37.2 mL, 37.2 mmol) at 0 °C, dropwise over 20 min. Reaction mixture was stirred for 2 h at rt under N2atmosphere (Reaction condition a). To the reaction mixture ice cold aq.NH4Cl (20 mL) was added drop wise at 0 °C, diluted with water and extracted with ethyl acetate (2 X 200 mL). Organic layer was dried using Na2S04and evaporated. The crude was purified by gradient column chromatography using 20% ethyl acetate in hexane to afford pink coloured solid (2) (4.1 g, 97% yield). MS (ESI): Mass calcd. for C9H8BrNO, m/z 226.07 found 228.0[M+H]2+.

References:

WO2019/77631,2019,A1 Location in patent:Paragraph 000133; 000332

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