Potassium Carbonate → 2'-Fluoro-4-nitro-biphenyl-3-carbaldehyde

HRID 506853Notes

Reaction equation

HRID 506853 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:7]=[O:8])[CH:9]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 972335-Bromo-2-nitrobenzaldehydeHCID 27343542-Fluorophenylboronic acid

Product 1

HCID 866341922'-Fluoro-4-nitro-biphenyl-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-bromo-2-nitrobenzaldehyde (8.2 g, 36 mmol), 2-fluorobenzeneboronic acid (10.0 g, 71.6 mmol) and 2M K2CO3 (54 mL) in dioxane (250 mL) was degassed with nitrogen. Pd(PPh3)4 (3.9 g, 3.6 mmol) was added, and the resulting mixture was degassed again and heated to reflux for 90 minutes. The resulting mixture was then diluted with EtOAc and washed with saturated aqueous NaHCO3 solution and brine. The EtOAc extract was dried with MgSO4, filtered, and concentrated in vacuo to yield a residue. The residue was purified by silica gel chromatography eluted with ethyl acetate and heptanes from 0:100 to 5:95 to yield a yellow solid.

Workup

  1. customthe resulting mixture was degassed again
  2. temperatureheated
  3. temperatureto reflux for 90 minutes
  4. additionThe resulting mixture was then diluted with EtOAc
  5. washwashed with saturated aqueous NaHCO3 solution and brine
  6. extractionThe EtOAc extract
  7. dry with materialwas dried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto yield a residue
  11. customThe residue was purified by silica gel chromatography
  12. washeluted with ethyl acetate and heptanes from 0:100 to 5:95
  13. customto yield a yellow solid

Sources & evidence

ORD record
ord-de33104ab4bc4ea1921e13225f58ae43
Source dataset
uspto-grants-2010_08
Patent number
US07786116B2

Reaction notes

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