Ethanol → Methyl 5'-fluoro-2'-nitrobiphenyl-2-carboxylate

HRID 1966494Notes

Reaction equation

HRID 1966494 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1B(O)O)=[O:4].Br[C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23].C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.C(O[Pd]OC(=O)C)(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[F:21][C:19]1[CH:18]=[CH:17][C:16]([N+:22]([O-:24])=[O:23])=[C:15]([C:6]2[C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:20]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27569932-Bromo-4-fluoro-1-nitrobenzeneHCID 27734962-(Methoxycarbonyl)benzeneboronic acid

Product 1

HCID 67296936Methyl 5'-fluoro-2'-nitrobiphenyl-2-carboxylateYield 56.9%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 6344DichloromethaneSolvent

Procedure

To a microwave vessel was added 2-(methoxycarbonyl)phenylboronic acid (63.4 mg, 0.352 mmol), 2-bromo-4-fluoro-1-nitrobenzene (77 mg, 0.35 mmol), diacetoxypalladium (0.93 mg, 4.1 mmol) and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (3.47 mg, 8.45 μmol). Ethanol (1760 μl) and sodium carbonate (176 μl, 0.352 mmol) were added and the mixture was reacted in a microwave reactor at 100° C. for 30 min. The reaction mixture was diluted with dichloromethane, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography (eluant: 9:1 hexane/ethyl acetate) to provide methyl 5′-fluoro-2′-nitrobiphenyl-2-carboxylate (37a, 54.8 mg, 0.199 mmol, 56.6% yield).

Workup

  1. customthe mixture was reacted in a microwave reactor at 100° C. for 30 min
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative thin layer chromatography (eluant: 9:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7cc4ca40e53e4282bbf71bf8066e04f1
Source dataset
uspto-grants-2013_04
Patent number
US08420596B2

Reaction notes

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