Sodium Carbonate → 4'-(Trifluoromethyl)-4-biphenylcarbaldehyde

HRID 2406915Notes

Reaction equation

HRID 2406915 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]([F:22])([F:21])[C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(O)CC>[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 707414-BromobenzaldehydeHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 27827124'-(Trifluoromethyl)-4-biphenylcarbaldehyde

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 10311-PropanolSolvent

Conditions

Temperature
70 °C

Procedure

A round bottom flask was charged with 4-bromobenzaldehyde (69.6 g, 376 mmol), 4-(trifluoromethyl)phenylboronic acid (75.0 g, 395 mmol) and 1-propanol (627 mL). The reaction mixture was stirred for 15 minutes at 70° C. until a clear solution was obtained. The resulting solution was treated with triphenylphosphine (888 mg, 3.38 mmol), palladium(II) acetate (256 mg, 1.13 mmol), 2M sodium carbonate (226 mL, 451 mmol) and water (138 mL). The reaction was heated at reflux for 1 hour, open to air. Water (900 mL) was then added and the reaction was cooled to 7° C. in an ice bath. The reaction was thoroughly stirred for 30 minutes until the title compound precipitated out. The mixture was then filtered and the solid washed with cold water (˜600 mL). The solid was then solubilized in diethylether (500 mL) and filtered through a pad of celite and silica, rinsing with diethylether (2×500 mL). Removal of the solvent under reduced pressure afforded 4′-(trifluoromethyl) biphenyl-4-carbaldehyde (90.0 g, 96%) as a pure white solid. 1H NMR (400 MHz, CDCl3, δ): 7.75 (s, 4 H) 7.76-7.79 (m, 2 H) 7.96-8.04 (m, 2 H) 10.10 (s, 1 H). MS (M+1): 250.3.

Workup

  1. customwas obtained
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 1 hour, open to air
  4. temperaturethe reaction was cooled to 7° C. in an ice bath

Sources & evidence

ORD record
ord-f323582e6556484f852b6c43e9fce55b
Source dataset
uspto-grants-2014_08
Patent number
US08809342B2

Reaction notes

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