Diethyl Malonate → HCID 21779975, compound

HRID 50857Notes

Reaction equation

HRID 50857 reaction equation
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Br[CH2:15][C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[CH:18][C:17]=1[F:25]>CN(C=O)C.C1COCC1>[F:25][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([N+:22]([O-:24])=[O:23])[C:16]=1[CH2:15][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 747792-(Bromomethyl)-1-fluoro-3-nitrobenzene

Product 1

HCID 21779975HCID 21779975, compoundYield 123.6%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent2×

Procedure

To a suspension of NaH (5.2 g, 130 mmol) in DMF/THF (110 ml/45 ml) was added diethyl malonate (19 ml, 125 mmol) dropwise and the mixture was stirred for 30 min at room temperature. To the mixture was added 2-(Bromomethyl)-1-fluoro-3-nitrobenzene (29 g, 124 mmol) in DMF/THF (40 ml/30 ml) and the resulting mixture was refluxed for 3 h. After cooling, the excess reagent was quenched with brine and the mixture was extracted with ethyl acetate. The extract was dried over sodium sulfate and concentrated in vacuo to afford diethyl 2-(2-Fluoro-6-nitrobenzyl)malonate (48 g) as a brown oil. This crude product was used in the next step without further purification.

Workup

  1. temperaturethe resulting mixture was refluxed for 3 h
  2. temperatureAfter cooling
  3. customthe excess reagent was quenched with brine
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe extract was dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3115178dc1e4428786be33bc2413f7c8
Source dataset
uspto-grants-2004_03
Patent number
US06713490B2

Reaction notes

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