4-Fluorobenzamide → HCID 10705737, compound

HRID 2300593Notes

Reaction equation

HRID 2300593 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.Br[CH:12]([CH3:20])[C:13](=O)[CH2:14][C:15]([O:17][CH3:18])=[O:16]>C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:18][O:17][C:15](=[O:16])[CH2:14][C:13]1[N:8]=[C:6]([C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)[O:7][C:12]=1[CH3:20]

Participants

5

Reactant 2

HCID 715724-FluorobenzamideHCID 9815681Methyl 4-bromo-3-oxopentanoate

Product 1

HCID 10705737HCID 10705737, compoundYield 25.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 667 mg (4.80 mmol) of 4-fluorobenzamide and 1.0 g (4.80 mmol) of methyl 4-bromo-3-oxo-pentanoate in 6 mL of dry toluene was heated at 120° C. for 16 h. The resulting dark slurry was cooled to rt, diluted with 10 mL of EtOAc, and washed with NaHCO3 (1×10 mL). The organic layer was separated, dried (MgSO4), and the solvents removed under reduced pressure. Purification of the material by silica gel flash column chromatography using hexane/EtOAc 4/1 as eluent to afford 308 mg of the title compound as a clear oil: 1H NMR (CDCl3, 400 MHz) δ7.97 (m, 2H), 7.11 (m, 2H), 3.73 (s, 3H), 3.56 (s, 2H), 2.36(s, 3H).

Workup

  1. washwashed with NaHCO3 (1×10 mL)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. customthe solvents removed under reduced pressure
  5. customPurification of the material by silica gel flash column chromatography

Sources & evidence

ORD record
ord-d9f95af6b12d46738904fefc13f1afd9
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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