2,4-Difluoroacetophenone → 2,4-difluoro-N-octyl-beta-oxo-benzenepropanamide

HRID 1198047Notes

Reaction equation

HRID 1198047 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[CH2:12]([N:20]=[C:21]=[O:22])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C([N-]C(C)C)(C)C.[Li+]>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH2:10][C:21]([NH:20][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:22]

Participants

4

Reactant 3

HCID 677702,4-DifluoroacetophenoneHCID 76616Octyl isocyanateHCID 2724682Lithium diisopropylamide

Product 1

HCID 191055872,4-difluoro-N-octyl-beta-oxo-benzenepropanamideYield 42.6%

Procedure

The title compound was prepared from 2',4'-difluoroacetophenone (5.0 g, 0.032 mol), octyl isocyanate (4.97 g, 0.032 mol), and lithium diisopropylamide (0.032 mol) using the procedure described in Example 1. Purification by flash chromatography (silica gel, 20% EtoAc/hexane) yielded 4.25 g (0.013 mol, 42.6%) of the desired product.

Workup

  1. customPurification by flash chromatography (silica gel, 20% EtoAc/hexane)

Sources & evidence

ORD record
ord-fa21657dea704b76b15b893bf8205caa
Source dataset
uspto-grants-1994_01
Patent number
US05278326

Reaction notes

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