2-Bromo-4-methylanisole → 4,5-dichloro-3-hydroxy-3-(2-methoxy-5-methylphenyl)-1,3-dihydro-2H-indol-2-one

Reaction equation

Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[Cl:11][C:12]1[C:20]([Cl:21])=[CH:19][CH:18]=[C:17]2[C:13]=1[C:14](=[O:23])[C:15](=[O:22])[NH:16]2>>[Cl:11][C:12]1[C:20]([Cl:21])=[CH:19][CH:18]=[C:17]2[C:13]=1[C:14]([OH:23])([C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10])[C:15](=[O:22])[NH:16]2

Participants

Reactant 2

HCID 891432-Bromo-4-methylanisole

HCID 51399804,5-Dichloro-1H-indole-2,3-dione

Product 1

HCID 231207064,5-dichloro-3-hydroxy-3-(2-methoxy-5-methylphenyl)-1,3-dihydro-2H-indol-2-oneYield 52.4%

Procedure

With 3.02 g of 2-bromo-1-methoxy-4-methyl benzene and 1.50 g of 4,5-dichloroisatin as starting materials, 1.23 g of the title compound (yellow solid) was obtained by a similar method to Step 21-1.

Sources & evidence

ORD record: ord-0dc6a4f4d3a04484ac6f759c8da195ae
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030499B2

Reaction notes

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