4-Nitrophenol → HCID 67069940, compound

HRID 2390824Notes

Reaction equation

HRID 2390824 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:5]([O:10][CH3:11])=[C:6]([CH2:8]Br)[CH:7]=1.[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)([O-:18])=[O:17].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][O:25][C:22]2[CH:23]=[CH:24][C:19]([N+:16]([O-:18])=[O:17])=[CH:20][CH:21]=2)[C:5]([O:10][CH3:11])=[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:3]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 67069911HCID 67069911, compound

Product 1

HCID 67069940HCID 67069940, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

step 2—A mixture of 114 (0.20 g, 0.59 mmol), 4-nitrophenol (0.082 g, 0.59 mmol) and K2CO3 (0.12 g, 0.89 mmol) in DMF was stirred at 50° C. for 2 h. The mixture was cooled to RT and partitioned between water and Et2O. The ether layer was concentrated, and the crude residue was purified by SiO2 chromatography eluting with EtOAc/hexane to afford 0.19 g (83%) of 5-bromo-1-tert-butyl-2-methoxy-3-(4-nitro-phenoxymethyl)benzene (116) as a white solid.

Workup

  1. temperatureThe mixture was cooled to RT
  2. custompartitioned between water and Et2O
  3. concentrationThe ether layer was concentrated
  4. customthe crude residue was purified by SiO2 chromatography
  5. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-bf4c0c0ce41246d88e237ab3064687c5
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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