Tetrahydrofuran → 4'-(Trifluoromethyl)-4-biphenylcarbaldehyde

HRID 1485051Notes

Reaction equation

HRID 1485051 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[CH:12]([C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)=[O:13].C(=O)([O-])[O-].[K+].[K+].O1CCCC1>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>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([C:17]2[CH:18]=[CH:19][C:14]([CH:12]=[O:13])=[CH:15][CH:16]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 5910734-Formylphenylboronic Acid

Product 1

HCID 27827124'-(Trifluoromethyl)-4-biphenylcarbaldehydeYield 108.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Conditions

Temperature
85 °C

Procedure

A mixture of 4-bromobenzotrifluoride (10.0 g), 4-formylphenylboronic acid (7.33 g), tetrakis(triphenylphosphine)palladium(0) (308 mg), potassium carbonate (30.7 g), tetrahydrofuran (300 mL) and water (100 mL) was stirred at 85° C. for 2 hours. After cooling the reaction mixture to room temperature, water was added to it, which was then extracted with ethyl acetate twice and the combined organic layers were washed with saturated brine. After adding anhydrous magnesium sulfate to the organic layers, the desiccant was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in n-hexane (60 mL) with heating and thereafter cooled to 0° C. The resulting precipitate was recovered by filtration to give the titled compound as a gray solid (12.1 g).

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. extractionwas then extracted with ethyl acetate twice
  3. washthe combined organic layers were washed with saturated brine
  4. additionAfter adding anhydrous magnesium sulfate to the organic layers
  5. customthe desiccant was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. dissolutionThe resulting residue was dissolved in n-hexane (60 mL)
  8. temperaturewith heating
  9. temperaturecooled to 0° C
  10. filtrationThe resulting precipitate was recovered by filtration

Sources & evidence

ORD record
ord-ba23d3b5ef4344faaf1fd36362994468
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

Loading…