Acetonitrile → Benzyl 2-(3-fluoro-4-nitrobenzamido)acetate

HRID 1399450Notes

Reaction equation

HRID 1399450 reaction equation
[F-:1].[K+].I([C:6]1[CH:7]=[C:8]([CH:23]=[CH:24][C:25]=1[N+:26]([O-:28])=[O:27])[C:9]([NH:11][CH2:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])=[O:10])(=O)=O.C1OCCOCCOCCOCCOCCOC1.C(#N)C>CCOC(C)=O>[F:1][C:6]1[CH:7]=[C:8]([CH:23]=[CH:24][C:25]=1[N+:26]([O-:28])=[O:27])[C:9]([NH:11][CH2:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])=[O:10]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 86713123Benzyl 2-(3-iodyl-4-nitrobenzamido)acetate

Product 1

HCID 86713122Benzyl 2-(3-fluoro-4-nitrobenzamido)acetateYield 61%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of spray-dried KF (614 mg, 10.59 mmol), intermediate 7 (1 g, 2.12 mmol), 18-crown-6 (40 mg) and dry acetonitrile (20 mL) was refluxed for 40 min. After completion of reaction (TLC), the mixture was diluted with EtOAc (75 mL). The solution was successively washed with water (50 mL) and brine (50 mL) and dried over anhyd Na2SO4. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using chloroform:hexane (75:25) as eluents to give the product as a colorless solid (430 mg, 61%), mp 118-120° C. 1H NMR (400 MHz, CDCl3): δ 8.13 (1H, t, J=7.8 Hz), 7.75 (1H, d, J=10.8 Hz), 7.68 (1H, d, J=8.0 Hz), 7.38 (5H, br s), 6.68 (1H, br s), 5.25 (2H, s), 4.29 (2H, d, J=4.8 Hz); LC-MS negative ion mode): m/z 331 (M−H)−.

Workup

  1. temperaturewas refluxed for 40 min
  2. customAfter completion of reaction (TLC)
  3. washThe solution was successively washed with water (50 mL) and brine (50 mL)
  4. dry with materialdried over anhyd Na2SO4
  5. filtrationThe solution was filtered
  6. customevaporated the solvent
  7. customThe residue was chromatographed over silica gel column

Sources & evidence

ORD record
ord-bd08398fce0a47cfa060711fdbaaa270
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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