Hydrochloric Acid → 1,3-Diethyl 2-(3-fluoro-2-nitrophenyl)propanedioate

HRID 2173271Notes

Reaction equation

HRID 2173271 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N+:9]([O-:11])=[O:10].C([O-])([O-])=O.[K+].[K+].[C:18]([O:26][CH2:27][CH3:28])(=[O:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].Cl>CN(C=O)C.C(OCC)C>[F:8][C:4]1[C:3]([N+:9]([O-:11])=[O:10])=[C:2]([CH:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:18]([O:26][CH2:27][CH3:28])=[O:25])[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 11430Potassium CarbonateHCID 879221,3-Difluoro-2-nitrobenzene

Product 1

HCID 579311071,3-Diethyl 2-(3-fluoro-2-nitrophenyl)propanedioate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 1,3-difluoro-2-nitrobenzen (5.0 g, 31.4 mmol) in 50 mL of dry DMF was added K2CO3 (4.41 g, 32 mmol) and diethyl malonate (3.6 mL, 31.4 mmol). The reaction mixture was heated to 65° C. and stirred for 24 hours. After cooling to room temperature, the mixture was neutralized with 2 N HCl and extrated with diethyl ether. The ether layer was dried over anhydrous sodium sulfate and concentrated. The crude product was purified via column chromatograph to afford diethyl (3-fluoro-2-nitrophenyl)propanedioate. 1H-NMR (400 MHz, CDCl3) δ 7.50˜7.55 (m, 1H), 7.38˜7.40 (rn, 1H), 7.23˜7.28 (m, 1H), 4.82 (s, 1H), 3.77 (s, 6H).

Workup

  1. temperatureAfter cooling to room temperature
  2. dry with materialThe ether layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified via column chromatograph

Sources & evidence

ORD record
ord-04a94cd465004eb2aa03ad388a5a38c4
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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