Hydrochloric Acid → 4-Cyclopentyl-3-(trifluoromethyl)benzonitrile

HRID 217471Notes

Reaction equation

HRID 217471 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].CN1CCCC1=O.[CH:21]1([Mg]Br)[CH2:25][CH2:24][CH2:23][CH2:22]1.Cl>C1COCC1.C(OCC)C.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Fe]>[CH:21]1([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[C:10]([F:13])([F:12])[F:11])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 27364744-Chloro-3-(trifluoromethyl)benzonitrileHCID 178419650HCID 178419650, compound

Product 1

HCID 592144344-Cyclopentyl-3-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 3

HCID 11110968Iron (III) acetylacetonateCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-chloro-3-(trifluoromethyl)benzonitrile (1.5 g), iron (III) acetylacetonate (130 mg), and 1-methylpyrrolidin-2-one (4 mL) in THF (45 mL) was added a 1 M solution of cyclopentyl magnesium bromide in THF (8.8 mL) at 5° C., followed by stirring at room temperature for 0.5 hours and diluting with diethylether. 1 M hydrochloric acid was slowly added thereto, followed by extraction with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:EtOAc=100:0 to 95:5) to obtain 4-cyclopentyl-3-(trifluoromethyl)benzonitrile (367 mg) as a white solid.

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:EtOAc=100:0 to 95:5)

Sources & evidence

ORD record
ord-35b866f798f740aebaad3a0c86cb4316
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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