Dimethylformamide → 2-Chloro-4-(1-pyrrolidinylmethyl)benzaldehyde

HRID 514591Notes

Reaction equation

HRID 514591 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][C:3]=1[Cl:14].[Li]CCCC.CN([CH:23]=[O:24])C>C1COCC1.CCCCCC>[Cl:14][C:3]1[CH:4]=[C:5]([CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][C:2]=1[CH:23]=[O:24]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 58258314HCID 58258314, compoundHCID 178418339Butyllithium

Product 1

HCID 582584922-Chloro-4-(1-pyrrolidinylmethyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Reaction under N2 atmosphere. A solution of 1-[(4-bromo-3-chlorophenyl)methyl]-pyrrolidine (25.8 g, 93.96 mmol) in THF (200 ml) was stirred at −78° C. for 15 min A 2.5 M n-BuLi solution in hexane was added to the mixture over a period of 15 min. After 30 min, a solution of DMF (7.3 ml, 93.96 mmol) in THF (50 ml) was added dropwise to the mixture. The reaction temperature was allowed to rise to r.t. slowly, and the mixture was stirred overnight. The reaction was quenched by the addition of water at 0° C. The mixture was extracted with EtOAc (3×150 ml). The combined organic layer was washed with brine, dried (MgSO4), filtered and the solvent was evaporated in vacuo.

Workup

  1. customReaction under N2 atmosphere
  2. additionwas added to the mixture over a period of 15 min
  3. customto rise to r.t.
  4. customThe reaction was quenched by the addition of water at 0° C
  5. extractionThe mixture was extracted with EtOAc (3×150 ml)
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-e9cfd6c7537341048d48c197ace69fb2
Source dataset
uspto-grants-2015_08
Patent number
US09107946B2

Reaction notes

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