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

HRID 1638466Notes

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-8bf600d113764821ab05afe6816a97cb
Source dataset: uspto-grants-1989_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04879391

Reaction notes

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