Isopropyl iodide → HCID 54238943, compound

HRID 518853Notes

Reaction equation

HRID 518853 reaction equation
C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+].[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[C:15]=1[OH:23].I[CH:25]([CH3:27])[CH3:26]>CN(C)C=O>[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[C:15]=1[O:23][CH:25]([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 135454532-Bromo-6-nitrophenol

Product 1

HCID 54238943HCID 54238943, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.23 g of potassium carbonate, 14.6 g of caesium carbonate, 22 ml of dimethylformamide and 1.0 g of 2-bromo-6-nitrophenol are successively introduced into a three-necked round-bottomed flask under argon. The resulting suspension is stirred at ambient temperature for 10 min, and then 0.91 ml of 2-iodopropane is added in one go. The round-bottomed flask is rinsed with 10 ml of dimethylformamide and then the reaction mixture is heated at 40° C. for 48 h. After cooling to ambient temperature, the mixture is treated with 50 ml of water and extracted four times with 30 ml of ethyl acetate. The organic extracts are combined and washed with 30 ml of saturated brine and then 30 ml of water. The organic phase is then dried over magnesium sulfate and then concentrated to dryness under reduced pressure. The residue is purified by chromatography on a 30 g silica cartridge, elution being carried out with a 95/5 v/v cyclohexane/ethyl acetate mixture at a flow rate of 30 ml/min, so as to obtain 1.04 g of 1-bromo-2-isopropoxy-3-nitrobenzene in the form of a yellow oil.

Workup

  1. washThe round-bottomed flask is rinsed with 10 ml of dimethylformamide
  2. temperaturethe reaction mixture is heated at 40° C. for 48 h
  3. temperatureAfter cooling to ambient temperature
  4. additionthe mixture is treated with 50 ml of water
  5. extractionextracted four times with 30 ml of ethyl acetate
  6. washwashed with 30 ml of saturated brine
  7. dry with materialThe organic phase is then dried over magnesium sulfate
  8. concentrationconcentrated to dryness under reduced pressure
  9. customThe residue is purified by chromatography on a 30 g silica cartridge, elution

Sources & evidence

ORD record
ord-7de17287045b469687269bdc37d2ea37
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

Loading…