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

HRID 1110874Notes

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-eab50fdbf55c43ba91e908a2b793080d
Source dataset: uspto-grants-1990_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04977178

Reaction notes

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