Water → HCID 66757224, compound

HRID 660472Notes

Reaction equation

HRID 660472 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:12]([O:8][C:6]1[CH:7]=[C:2]([I:1])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 140916895-Iodo-2-nitrophenol

Product 1

HCID 66757224HCID 66757224, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 5-iodo-2-nitrophenol (2.65 g, 10 mmol) (J. Org. Chem. 1998, 63, 4199-4208) in DMF (10 mL) is added benzyl bromide (1.71 g, 10 mmol) and K2CO3 (2.07 g, 15 mmol) and the mixture is heated at 65° C. for 30 min. Then water is added (400 mL) and it is extracted by EtOAc (2×200 mL). The water layer is then acidified and extracted with EtOAc (100 mL). The combined EtOAc layer is then washed with 1N HCl and brine, dried with NaSO4 and concentrated to give the title compound as a yellow solid.

Workup

  1. extractionis extracted by EtOAc (2×200 mL)
  2. extractionextracted with EtOAc (100 mL)
  3. washThe combined EtOAc layer is then washed with 1N HCl and brine
  4. dry with materialdried with NaSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c029fab11a594a5e8f615d0d05f3c7ce
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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