1-Nitropropane → Tert-butyl 2-fluoro-5-(1-nitropropyl)benzoate

HRID 554762Notes

Reaction equation

HRID 554762 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1C)(C)(C)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[N+:46]([CH2:49][CH2:50][CH3:51])([O-:48])=[O:47]>C(COC)OC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:15][C:5]1[CH:4]=[CH:3][C:2]([CH:49]([N+:46]([O-:48])=[O:47])[CH2:50][CH3:51])=[CH:14][C:6]=1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

7

Reactant 4

HCID 79031-NitropropaneHCID 62657Potassium Phosphate, TribasicHCID 27349372-(Di-tert-butylphosphino)-2'-methyl-1,1'-biphenylHCID 63896644Tert-butyl 5-bromo-2-fluorobenzoate

Product 1

HCID 86246594Tert-butyl 2-fluoro-5-(1-nitropropyl)benzoate

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To tert-butyl 5-bromo-2-fluorobenzoate (1.26 g) in dimethoxyethane (22.9 ml) solution, tris(dibenzylideneacetone)dipalladium (0.10 g), 2-(di-tert-butylphosphino)-2′-methylbiphenyl (0.14 g), tripotassium phosphate (1.07 g), and 1-nitropropane (0.82 ml) were added, the mixture was stirred at room temperature for 1 minute, then the mixture was stirred under heating and reflux for 15 hours. The insoluble compound was filtered out, then the filtrate was concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate, ethyl acetate: 0 to 10%) to obtain the title compound (392 mg).

Workup

  1. stirringthe mixture was stirred
  2. temperatureunder heating
  3. temperaturereflux for 15 hours
  4. filtrationThe insoluble compound was filtered out
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate, ethyl acetate: 0 to 10%)

Sources & evidence

ORD record
ord-fc3311173c4c46cab15641825b7beab9
Source dataset
uspto-grants-2011_11
Patent number
US08049006B2

Reaction notes

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