2-Nitrophenol → 1-Cyclopentyl-4-((4-nitrophenoxy)methyl)-2-(trifluoromethyl)benzene

HRID 2040591Notes

Reaction equation

HRID 2040591 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1O)([O-:3])=[O:2].[C:11](=[O:14])([O-])[O-].[K+].[K+].ClC[C:19]1[CH:24]=[CH:23][C:22]([CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[C:21]([C:30]([F:33])([F:32])[F:31])[CH:20]=1>CC(N(C)C)=O>[CH:25]1([C:22]2[CH:23]=[CH:24][C:19]([CH2:11][O:14][C:7]3[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)=[CH:20][C:21]=2[C:30]([F:31])([F:32])[F:33])[CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 11430Potassium CarbonateHCID 534026024-(Chloromethyl)-1-cyclopentyl-2-(trifluoromethyl)benzene

Product 1

HCID 672205701-Cyclopentyl-4-((4-nitrophenoxy)methyl)-2-(trifluoromethyl)benzeneYield 85%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
77 °C

Procedure

In a 1 L flask equipped with a stirrer, thermocouple, condenser and a nitrogen inlet, was placed nitrophenol (28 g, 201 mmol) in DMA (150 mL) and potassium carbonate powder (28.7 g, 207 mmol). 4-(Chloromethyl)-1-cyclopentyl-2-(trifluoromethyl)benzene (45.4 g, 173 mmol) was added and washed in with DMA (120 mL). The reaction was heated at 80° C. (bath, internal 77° C.) overnight. The mixture was cooled and poured into ice water (1 L). The solids formed were allowed to settle with stirring for 4 h and collected by filtration. The solid collected was stirred in sodium bicarbonate solution (300 mL), filtered, washed with water, and air dried. The pale yellow residue was washed with hexanes (250 mL) and the solids were dried in vacuum oven overnight to give the title compound (41.4 g, ˜85% pure by LC). LCMS m/z=366.2 [M+H]+.

Workup

  1. customIn a 1 L flask equipped with a stirrer
  2. customthermocouple, condenser and a nitrogen inlet, was placed
  3. washwashed in with DMA (120 mL)
  4. temperatureThe mixture was cooled
  5. additionpoured into ice water (1 L)
  6. customThe solids formed
  7. filtrationcollected by filtration
  8. customThe solid collected
  9. stirringwas stirred in sodium bicarbonate solution (300 mL)
  10. filtrationfiltered
  11. washwashed with water, and air
  12. customdried
  13. washThe pale yellow residue was washed with hexanes (250 mL)
  14. customthe solids were dried in vacuum oven overnight

Sources & evidence

ORD record
ord-76e453d3a9f74109aa5bd0b0e95a04e6
Source dataset
uspto-grants-2013_11
Patent number
US08580841B2

Reaction notes

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