Cesium carbonate → 1-Benzyl-2-fluoro-3-nitro-benzene

HRID 1055384Notes

Reaction equation

HRID 1055384 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[F:11].[CH2:12]([B-](F)(F)F)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[K+].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:12]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[F:11])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 23692459Potassium benzyltrifluoroboranuideHCID 404274461-Bromo-2-fluoro-3-nitrobenzene

Product 1

HCID 900378141-Benzyl-2-fluoro-3-nitro-benzeneYield 62.5%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

To a mixture 1-bromo-2-fluoro-3-nitrobenzene (800 mg, 3.6 mmol), potassium benzyltrifluoroborate (2.2 g, 10.9 mmol) and Cs2CO3 (3.6 g, 10.9 mmol) in dioxane/H2O (10:1, 18 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (60 mg, 2 mol %) and the mixture was heated to 100° C. for 8 h. The mixture was cooled to RT, diluted with H2O and extracted with EtOAc. The combined extracts were washed with H2O, brine, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography to give the title compound (520 mg, 62%).

Workup

  1. temperatureThe mixture was cooled to RT
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b4797b8e6f7846b4b0072baf70901add
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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