Toluene → 4'-Fluorobiphenyl-4-carbaldehyde

HRID 1485052Notes

Reaction equation

HRID 1485052 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>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.O.C(O)C>[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 707414-BromobenzaldehydeHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 13925504'-Fluorobiphenyl-4-carbaldehydeYield 96.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromobenzaldehyde (10.0 g), 4-fluorophenylboronic acid (11.3 g), tetrakis(triphenylphosphine)palladium(0) (3.12 g), sodium carbonate (28.6 g), toluene (150 mL), ethanol (70.0 mL) and water (70.0 mL) was stirred at 100° C. for 12 hours. After cooling the reaction mixture to room temperature, water was added and extraction with toluene was conducted twice. The combined organic layers were washed with saturated brine and dried over anhydrous magnesium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10) and after adding n-hexane to the residue, the mixture was stirred. The precipitate was recovered by filtration and dried under reduced pressure to give the titled compound as a colorless solid (10.4 g).

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. extractionextraction with toluene
  3. washThe combined organic layers were washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe desiccant was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10)
  8. additionafter adding n-hexane to the residue
  9. stirringthe mixture was stirred
  10. filtrationThe precipitate was recovered by filtration
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-eba4a806730348c88dc12af58a7e8898
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

Loading…