o-Bromocumene → 5-chloro-3-hydroxy-3-(2-isopropylphenyl)-1,3-dihydro-2H-indol-2-one

HRID 1662616Notes

Reaction equation

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

Participants

Reactant 2

HCID 23475o-Bromocumene

HCID 872035-chloro-1H-indole-2,3-dione

Product 1

HCID 231207095-chloro-3-hydroxy-3-(2-isopropylphenyl)-1,3-dihydro-2H-indol-2-oneYield 98.3%

Procedure

With 8.2 g of 1-bromo-2-isopropyl benzene and 3.0 g of 5-chloroisatin as starting materials, 4.9 g of the title compound (pale yellow amorphous) was obtained by a similar method to Step 21-1.

Sources & evidence

ORD record: ord-fa1ccbd87f584dc99317e5a700af163c
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030499B2

Reaction notes

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