4-Bromoanisole → 5-Chloro-3-hydroxy-3-(4-methoxyphenyl)-1,3-dihydro-2H-indol-2-one

HRID 31345

Reaction equation

HRID 31345 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.[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]>C1COCC1>[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:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 77304-BromoanisoleHCID 872035-chloro-1H-indole-2,3-dioneHCID 5462224Magnesium

Product 1

HCID 225609075-Chloro-3-hydroxy-3-(4-methoxyphenyl)-1,3-dihydro-2H-indol-2-oneYield 72.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

This compound is prepared according to the procedure described in step A of Preparation 1.3 starting with 3.5 g of magnesium, 25 g of 1-bromo-4-methoxybenzene, 50 ml of THF and a mixture of 8 g of 5-chloro-1H-indol-2,3-dione in 50 ml of THF. 9.3 g of the expected product are obtained after crystallization from hot iso ether; m.p.=202° C.

Workup

  1. customThis compound is prepared

Sources & evidence

ORD record
ord-86d7b71e15434408bfc215eb7ab4417b
Source dataset
uspto-grants-2008_09
Patent number
US07425566B2

Linked notes

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