Sodium Iodide → 1-(3-Nitro-4-phenylmethoxyphenyl)ethanone

HRID 1955783Notes

Reaction equation

HRID 1955783 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C([O-])([O-])=O.[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Na+].[I-]>C1(C)C=CC=CC=1.CN(C=O)C>[C:21]1([CH2:20][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=2[N+:11]([O-:13])=[O:12])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7498Benzyl Bromide2×HCID 11430Potassium CarbonateHCID 1387234-Hydroxy-3-Nitroacetophenone

Product 1

HCID 112657201-(3-Nitro-4-phenylmethoxyphenyl)ethanoneYield 84%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

To a mechanically stirred DMF (260 mL) suspension of 1-[4-hydroxy-3-nitrophenyl]ethanone (51 g, 282 mmol) and K2CO3 (17 g, 847 mmol) was added benzyl bromide (68 mL, 572 mmol) followed by NaI (47 g, 313 mmol). After stirring overnight at 20° C., an additional 10 mL of benzyl bromide was added and stirred 15 minutes. The reaction was quenched by the addition of 1.6 L water. The resulting suspension was stirred overnight and then filtered. The collected solids were washed 3×250 mL=750 mL water and dried in vacuo at ~55° C. to give 75 g crude product which was slurried in 1.3 L toluene at ~75° C., filtered hot through a 5.0 μm membrane, concentrated in vacuo to a volume of ~300 mL, diluted with 250 mL heptane, and the suspension cooled from ~60° C. to ambient. After filtration, the collected solids were washed with heptane and dried in vacuo at ~55° C. to give 64 g (84%) of the title compound.

Workup

  1. stirringstirred 15 minutes
  2. customThe reaction was quenched by the addition of 1.6 L water
  3. stirringThe resulting suspension was stirred overnight
  4. filtrationfiltered
  5. washThe collected solids were washed 3×250 mL=750 mL water
  6. customdried in vacuo at ~55° C.
  7. customto give 75 g crude product which
  8. filtrationfiltered hot through a 5.0 μm membrane
  9. concentrationconcentrated in vacuo to a volume of ~300 mL
  10. additiondiluted with 250 mL heptane
  11. temperaturethe suspension cooled from ~60° C.
  12. filtrationAfter filtration
  13. washthe collected solids were washed with heptane
  14. customdried in vacuo at ~55° C.

Sources & evidence

ORD record
ord-280c3d58500a4ae2a79e8d3088df0a0a
Source dataset
uspto-grants-1998_07
Patent number
US05776983

Reaction notes

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