Water → 3-Hydroxy-4,6-dichloro-1,3-dihydro-3-(4-trifluoromethylphenyl)indol-2-one

HRID 219762

Reaction equation

HRID 219762 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1.[Cl:13][C:14]1[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]2[C:15]=1[C:16](=[O:25])[C:17](=[O:24])[NH:18]2.O>C(OCC)C.C1COCC1>[OH:25][C:16]1([C:3]2[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=2)[C:15]2[C:19](=[CH:20][C:21]([Cl:23])=[CH:22][C:14]=2[Cl:13])[NH:18][C:17]1=[O:24]

Participants

7

Reactant 4

HCID 962WaterHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 2519084,6-DichloroisatinHCID 5462224Magnesium

Product 1

HCID 666026703-Hydroxy-4,6-dichloro-1,3-dihydro-3-(4-trifluoromethylphenyl)indol-2-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

1.8 g of Grignard magnesium are placed in 19 ml of anhydrous ethyl ether in a round-bottomed flask equipped with a mechanical stirrer, and under a stream of nitrogen. A mixture of 8.9 ml of 4-bromotrifluoromethylbenzene in 46 ml of anhydrous ethyl ether is then added. The mixture is stirred for one hour, followed by addition of a solution of 5.7 g of 4,6-dichloro-1H-indole-2,3-dione in 100 ml of anhydrous THF. The mixture is stirred at room temperature for 4 hours 30 minutes. Water is added and the resulting mixture is extracted with ethyl acetate. The organic phase is separated out and dried over Na2SO4, filtered and evaporated under vacuum. The residue is taken up in ethyl acetate and washed with 1N sodium hydroxide solution. The organic phase is dried over Na2SO4, filtered and evaporated under vacuum. The solid is taken up in ethyl ether and filtered off. 4.7 g of expected product are obtained.

Workup

  1. customequipped with a mechanical stirrer
  2. additionis then added
  3. stirringThe mixture is stirred at room temperature for 4 hours 30 minutes
  4. extractionthe resulting mixture is extracted with ethyl acetate
  5. customThe organic phase is separated out
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under vacuum
  9. washwashed with 1N sodium hydroxide solution
  10. dry with materialThe organic phase is dried over Na2SO4
  11. filtrationfiltered
  12. customevaporated under vacuum
  13. filtrationfiltered off

Sources & evidence

ORD record
ord-15e2988c599d4d829b0be32d5a2db277
Source dataset
uspto-grants-2012_06
Patent number
US08202871B2

Linked notes

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