Methyl acetoacetate → HCID 18000970, compound

HRID 478310Notes

Reaction equation

HRID 478310 reaction equation
[NH2:1][C:2]1[CH:7]([CH3:8])[O:6][CH2:5][C:4](=[O:9])[CH:3]=1.[Br:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[F:19])[CH:14]=O.[C:20]([O:26][CH3:27])(=[O:25])[CH2:21][C:22]([CH3:24])=O>C(O)C>[Br:10][C:11]1[CH:12]=[C:13]([CH:14]2[C:21]([C:20]([O:26][CH3:27])=[O:25])=[C:22]([CH3:24])[NH:1][C:2]3[CH:7]([CH3:8])[O:6][CH2:5][C:4](=[O:9])[C:3]2=3)[CH:16]=[CH:17][C:18]=1[F:19]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 18001001HCID 18001001, compound

Product 1

HCID 18000970HCID 18000970, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 88D (0.50 g, 3.9 mmol), 3-bromo-4-fluorobenzaldehyde 0.96 g, 4.7 mmol) and methyl acetoacetate (0.46 g, 3.9 mmol) in ethanol (4 mL) was heated to 80° C. in a sealed tube for 60 hours, cooled to ambient temperature and concentrated. The residue was chromatographed on silica gel eluting with 1% and then 2% methanol in dichloromethane to provide the title compound (0.97 g).

Workup

  1. concentrationconcentrated
  2. customThe residue was chromatographed on silica gel eluting with 1%

Sources & evidence

ORD record
ord-ef838dee85af4576b75ad2064a7bacc7
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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