Water → 1-(9,9-Di-n-butyl-7-nitrofluorene-2-yl)-ethanone

HRID 630644Notes

Reaction equation

HRID 630644 reaction equation
[CH2:1]([C:5]1([CH2:21][CH2:22][CH2:23][CH3:24])[C:17]2[CH:16]=[C:15]([N+:18]([O-:20])=[O:19])[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:2][CH2:3][CH3:4].[Cl-].[Al+3].[Cl-].[Cl-].[C:29](Cl)(=[O:31])[CH3:30].O>[N+](C1C=CC=CC=1)([O-])=O>[CH2:1]([C:5]1([CH2:21][CH2:22][CH2:23][CH3:24])[C:6]2[CH:7]=[C:8]([C:29](=[O:31])[CH3:30])[CH:9]=[CH:10][C:11]=2[C:12]2[C:17]1=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 444715309,9-Dibutyl-2-nitro-9H-fluorene

Product 1

HCID 1179383241-(9,9-Di-n-butyl-7-nitrofluorene-2-yl)-ethanoneYield 68.7%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent2×

Conditions

Temperature
45 °C

Procedure

After 7.0 g of 9,9-di-n-butyl-2-nitrofluorene (5) (21.7 mmol) was dissolved in 200 ml of anhydrous nitrobenzene and 5.77 g of anhydrous aluminum chloride (43.4 mmol) was added thereto, the reaction mixture was heated to 45° C., and a solution in which 3.40 g of acetyl chloride (43.3 mmol) was dissolved in 40 ml of anhydrous nitrobenzene was slowly added thereto for 1 hour, followed by stirring at 65° C. for 1 hour. Thereafter, the reaction mixture was cooled to room temperature, 100 ml of distilled water was added thereto and stirred for about 30 minutes, followed by extracting the product with 200 ml of dichloromethane. The extracted organic layer was sequentially washed with 100 ml of saturated aqueous sodium bicarbonate solution and 100 ml of distilled water. Then, a solid product obtained by drying the recovered organic layer over anhydrous magnesium sulfate and distilling a solvent under reduced pressure was dispersed in a small amount of ether and stirred at room temperature for 30 minutes, followed by filtering and drying, thereby obtaining 5.44 g of 1-(9,9-di-n-butyl-7-nitrofluorene-2-yl)-ethanone (6) (68.7%) as a light yellow product.

Workup

  1. additionwas slowly added
  2. temperatureThereafter, the reaction mixture was cooled to room temperature
  3. stirringstirred for about 30 minutes
  4. extractionby extracting the product with 200 ml of dichloromethane
  5. washThe extracted organic layer was sequentially washed with 100 ml of saturated aqueous sodium bicarbonate solution and 100 ml of distilled water
  6. customThen, a solid product obtained
  7. dry with materialby drying the recovered organic layer over anhydrous magnesium sulfate
  8. distillationdistilling a solvent under reduced pressure
  9. additionwas dispersed in a small amount of ether
  10. stirringstirred at room temperature for 30 minutes
  11. filtrationby filtering
  12. customdrying

Sources & evidence

ORD record
ord-9759c8c6ae0c4468b03633c03623c349
Source dataset
uspto-grants-2016_04
Patent number
US09316906B2

Reaction notes

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