Indole → 1-(4-methoxyphenyl)-1H-indole

HRID 1632656Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11]1.C([O-])([O-])=O.[K+].[K+]>>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)=[CH:3][CH:4]=1

Participants

Reactant 3

HCID 798Indole

HCID 77304-Bromoanisole

HCID 11430Potassium Carbonate

Product 1

HCID 7757151-(4-methoxyphenyl)-1H-indole

Procedure

By the method of Preparation C43, p-bromoanisole (140 g, 0.75 mole), indole (60 g, 0.51 mole), K2CO3 (75 g, 0.54 mole) and Cu2Br2 (28 g, 0.1 mole) were converted to title product, purified by distillation, rather than chromatography, 67.7 g, b.p. 150-160/0.4-0.5 mm, which crystallized on storage in the refrigerator, m.p. 52°-54° C.

Sources & evidence

ORD record: ord-fe7993308c014526b57ddb80d3f88033
Source dataset: uspto-grants-1984_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04476307

Reaction notes

Loading…