Dimethylformamide → 4-Cyclopentyl-3-(trifluoromethyl)benzaldehyde

HRID 62794Notes

Reaction equation

HRID 62794 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1.[Li]CCCC.CN([CH:25]=[O:26])C>C1COCC1>[CH:8]1([C:5]2[CH:6]=[CH:7][C:2]([CH:25]=[O:26])=[CH:3][C:4]=2[C:13]([F:16])([F:15])[F:14])[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 672111474-Bromo-1-cyclopentyl-2-(trifluoromethyl)benzeneHCID 178418339Butyllithium

Product 1

HCID 866538674-Cyclopentyl-3-(trifluoromethyl)benzaldehydeYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 15 mL round-bottomed flask were placed 4-bromo-1-cyclopentyl-2-(trifluoromethyl)benzene (0.186 g, 0.635 mmol) and anhydrous THF (1.86 mL) under argon atmosphere. The solution was stirred well and cooled to −78° C. (dry ice IPA bath). BuLi (2.5 M in hexanes, 0.281 mL, 0.703 mmol) was added in drops (slowly) and the reaction mixture was stirred at low temperature for 25 min. Anhydrous DMF (0.1 mL, 0.766 mmol) was added in drops at −78° C. (slowly). The mixture was stirred at −78° C. for 20 min then at room temperature for 30 min. The reaction was quenched with water, acidified with 2 M HCl and extracted with EtOAc. The EtOAc layer was washed with water, dried over Na2SO4, and concentrated in vacuo to give the title compound as an oil (60 mg). LCMS m/z=243.3 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.55-1.7 (m, 4H), 1.79-1.94 (m, 2H), 1.95-2.09 (m, 2H), 3.29-3.37 (m, 1H), 7.86 (d, J=8 Hz, 1H), 8.12 (d, J=8 Hz, 1H), 8.16 (d, J=12 Hz, 1H), 10.46 (s, 1H).

Workup

  1. customIn a 15 mL round-bottomed flask were placed
  2. stirringwas stirred at low temperature for 25 min
  3. stirringThe mixture was stirred at −78° C. for 20 min
  4. customThe reaction was quenched with water
  5. extractionextracted with EtOAc
  6. washThe EtOAc layer was washed with water
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-123487eb4442454db1c1c425420a18dc
Source dataset
uspto-grants-2016_09
Patent number
US09447041B2

Reaction notes

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