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

HRID 2173776Notes

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

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, 4H) 7.76-7.79 (m, 2H) 7.96-8.04 (m, 2H) 10.10 (s, 1H). MS (M+1): 250.3.

Workup

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

Sources & evidence

ORD record: ord-afca43d01dd24ba08aa4c696093c38ad
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056834B2

Reaction notes

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