1-(2-(Trifluoromethyl)phenyl)cyclopentanol → 1-Cyclopentyl-2-(trifluoromethyl)benzene

HRID 707754Notes

Reaction equation

HRID 707754 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1(O)[CH2:13][CH2:12][CH2:11][CH2:10]1.[H][H]>C(O)C.[Pd]>[CH:9]1([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:2]([F:1])([F:15])[F:16])[CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 628021401-(2-(Trifluoromethyl)phenyl)cyclopentanolHCID 178418361HCID 178418361, compound

Product 1

HCID 591465321-Cyclopentyl-2-(trifluoromethyl)benzeneYield 90.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-(2-(trifluoromethyl)phenyl)cyclopentanol (5.1 g, 22.15 mmol) in ethanol (32 mL) was added 10% Pd—C (500 mg; Degussa; wet) and the mixture was hydrogenated overnight with a hydrogen balloon. The reaction mixture was filtered through Celite®. The filtrate was poured into ice-water (100 mL) and extracted with CH2Cl2 (2×70 mL). The combined CH2Cl2 layer was washed with water (1×75 mL), dried over Na2SO4, filtered and the solvent was removed under reduced pressure to give the title compound (4.3 g). 1H NMR (400 MHz, CDCl3) δ ppm 1.58-1.67 (m, 4H), 1.81-1.90 (m, 2H), 2.06-2.15 (m, 2H), 3.32-3.43 (m, 1H), 7.22-7.26 (m, 1H), 7.45-7.51 (m, 2H), 7.58 (d, J=8 Hz, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. additionThe filtrate was poured into ice-water (100 mL)
  3. extractionextracted with CH2Cl2 (2×70 mL)
  4. washThe combined CH2Cl2 layer was washed with water (1×75 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a9de6fedb99444c583d1324c98a8e43e
Source dataset
uspto-grants-2015_11
Patent number
US09175320B2

Reaction notes

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