Water → HCID 68456703, compound

HRID 2197924Notes

Reaction equation

HRID 2197924 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH:12]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)([CH3:14])[CH3:13].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([O:21][C:18]2[CH:19]=[CH:20][C:15]([CH:12]([CH3:14])[CH3:13])=[CH:16][CH:17]=2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 74654-IsopropylphenolHCID 11430Potassium CarbonateHCID 27949042-Bromo-5-chloronitrobenzene

Product 1

HCID 68456703HCID 68456703, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1-Bromo-4-chloro-2-nitrobenzene (12 g, 50.7 mmol) was added to a solution of 4-isopropylphenol (8.3 g, 60.8 mmol), and K2CO3 (14.0 g, 101 mmol) in DMF (70 mL). The mixture was heated at 80° C. for 16 h. The reaction was poured into water. The aqueous phase was extracted with ethyl acetate and the combined phases were washed with water, brine, and dried over sodium sulfate, filtered and concentrated under vacuum giving the crude title compound. The crude product was purified by silica gel chromatography eluting with (hexanes/ethyl acetate 90:10) to give the title compound (13.5 g, 92%).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. washthe combined phases were washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customgiving the crude title compound
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with (hexanes/ethyl acetate 90:10)

Sources & evidence

ORD record
ord-0eb326e658504372ae4772c6a84d3b5d
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

Loading…