Benzene, 1-bromo-2-(trifluoromethyl)- → HCID 21925408, compound

HRID 1243322Notes

Reaction equation

HRID 1243322 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([F:12])([F:11])[F:10].[Cl:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18](=[O:23])[C:17]2=[O:24]>CCOCC.C1COCC1.II>[Cl:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18](=[O:23])[C:17]2([OH:24])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([F:12])([F:11])[F:10]

Participants

7

Reactant 3

HCID 9806Benzene, 1-bromo-2-(trifluoromethyl)-HCID 872035-chloro-1H-indole-2,3-dioneHCID 5462224Magnesium

Product 1

HCID 21925408HCID 21925408, compoundYield 32.6%

Reagents, catalysts & solvents 3

HCID 807IodineCatalystHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.3 g of magnesium and 0.01 g of iodine in 20 ml of ether is heated to reflux, a solution of 26 g of 1-bromo-2-trifluoromethylbenzene in 20 ml of ether is added dropwise and the resulting mixture is refluxed for 60 minutes. A solution of 9 g of 5-chloro-1H-indole-2,3-dione in 40 ml of THF is then added and refluxing is continued for 30 minutes. After cooling to RT, the reaction mixture is poured into an ice/concentrated HCl mixture and extracted with ether, the organic phase is washed with 1N NaOH solution and with water, and dried over Na2SO4, and the solvent is evaporated off under vacuum. 5.3 g of the expected product are obtained after crystallization from heptane, m.p.=205–208° C.

Workup

  1. temperatureis heated
  2. temperatureto reflux
  3. temperaturethe resulting mixture is refluxed for 60 minutes
  4. temperaturerefluxing
  5. extractionextracted with ether
  6. washthe organic phase is washed with 1N NaOH solution and with water
  7. dry with materialdried over Na2SO4
  8. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-e1fcce99fa9a42a3b693dedef61c41bb
Source dataset
uspto-grants-2006_10
Patent number
US07119086B2

Reaction notes

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