Hydrochloric Acid → HCID 66985342, compound

HRID 2191540Notes

Reaction equation

HRID 2191540 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH2:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:3]=1[F:14].[N+:15]([CH:18]([CH3:20])[CH3:19])([O-:17])=[O:16].C1CCN2C(=NCCC2)CC1.Cl>CC#N>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:13][C:18]([CH3:20])([N+:15]([O-:17])=[O:16])[CH3:19])[C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:3]=1[F:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3982-NitropropaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 66985257HCID 66985257, compound

Product 1

HCID 66985342HCID 66985342, compoundYield 106.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 2-(4-chloro-3-fluorophenyl)acrylate (1.00 g, 4.66 mmol) and 2-nitropropane (502 uL, 5.59 mmol) were dissolved in MeCN (16 mL) and treated with DBU (835 uL, 5.59 mmol) at room temperature. The mixture was allowed to stir over the weekend to completion. The mixture was poured into 1M HCl solution and extracted with ethyl acetate (2×). The combined organic portions were washed with water (1×), then brine, separated, dried over MgSO4, filtered, and concentrated in vacuo to yield methyl 2-(4-chloro-3-fluorophenyl)-4-methyl-4-nitropentanoate (1.51 g).

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. washThe combined organic portions were washed with water (1×)
  3. custombrine, separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8470837842164a86be9a3a05ca14a620
Source dataset
uspto-grants-2012_12
Patent number
US08329701B2

Reaction notes

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