5-Chlorooxindole → 3-(3-Bromo-5-tert-butyl-4-hydroxybenzylidene)-5-chloro-1,3-dihydroindol-2-one

HRID 2120226Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[Br:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=1[OH:21])[CH:16]=O>>[Br:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=1[OH:21])[CH:16]=[C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=2)[NH:7][C:6]1=[O:11]

Participants

Reactant 2

HCID 1528015-Chlorooxindole

HCID 148392973-Bromo-5-tert-butyl-4-hydroxybenzaldehyde

Product 1

HCID 537045623-(3-Bromo-5-tert-butyl-4-hydroxybenzylidene)-5-chloro-1,3-dihydroindol-2-oneYield 81%

Procedure

5-Chloro-2-oxindole (167 mg, 1 mmol) was condensed with 3-bromo-5-tert-butyl-4-hydroxybenzaldehyde (308.5 mg, 1.2 mmol) using method B to give 329 mg (81%) of 3-(3-bromo-5-tert-butyl-4-hydroxybenzylidene)-5-chloro-1,3-dihydroindol-2-one as a mixture of isomers.

Sources & evidence

ORD record: ord-d1448677acde436da318603a5dd419b6
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06689806B1

Reaction notes

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