Ethyl Bromide → 4-Ethoxy-1H-indole

HRID 992350Notes

Reaction equation

[H-].[Na+].[OH:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2.Br[CH2:14][CH3:15]>CN(C=O)C>[CH2:14]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)[CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

An oven dried two neck flask was charged with 5 ml DMF and NaH (66 mg, 60% in oil, 1.65 mmol). The mixture was cooled down to 0° C., followed by dropwise addition of 4-hydroxy indole (200 mg, 1.5 mmol) in 5 ml DMF over 10 second. After stirring for 30 min under N2, bromoethane in 2 ml DMF was added dropwise, and the reaction was allowed to warm to rt. with continued stirring for 2 hr. Removal of the solvent in vacuo, followed by aqueous work up afforded crude 4-ethoxyindole which was purified by prep. HPLC to afford 201 mg (83%) of pure 4-ethxyindole; HPLC retention time, 1.190 min.

Workup

customAn oven dried two neck flask
temperatureto warm to rt
stirringwith continued stirring for 2 hr
customRemoval of the solvent in vacuo

Sources & evidence

ORD record: ord-e0fd77c0b1b44a78abab0ce011b61f46
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06469006B1

Reaction notes

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