Benzene, 1-bromo-2-(trifluoromethyl)- → 2'-TrifluoroMethyl-Biphenyl-4-Carbaldehyde

HRID 710375Notes

Reaction equation

HRID 710375 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1Br.B(O)O.[C:15]([O-:18])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.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:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:3]1[CH:8]=[CH:7][C:6]([CH:15]=[O:18])=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 9806Benzene, 1-bromo-2-(trifluoromethyl)-HCID 10340Sodium CarbonateHCID 61668Boronic Acid

Product 1

HCID 13926532'-TrifluoroMethyl-Biphenyl-4-CarbaldehydeYield 177.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 2-trifluoromethyl-bromobenzene (0.7 g, 2.75 mmol) and 4-carbaldehyde boronic acid (0.5 g, 3.3 mmol) in dioxane (20 mL) under nitrogen at 80° C. was added Pd(PPh3)4 (0.05 g) followed by the addition of a solution of Na2CO3 (0.7 g) in H2O (5 m). The mixture was stirred at 100° C. for 6 h. The solvent was evaporated and the residue was diluted to 50 ml with EtOAc and washed with H2O. The solvent was evaporated to dryness and the residue was purified by FCC (SiO2) to give the title compound (0.61 g; 88%), as creamy solid. 1H-NMR (CDCl3) 7.49 (d, 1H, J=7.41 Hz); 7.48 (d, 2H, J=8.13 Hz); 7.61-7.53 (m, 2H); 7.76 (d, 1H, J=7.8 Hz); 7.91 (d, 2H, J=8.34 Hz); 10.07 (s, 1H).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted to 50 ml with EtOAc
  3. washwashed with H2O
  4. customThe solvent was evaporated to dryness
  5. customthe residue was purified by FCC (SiO2)

Sources & evidence

ORD record
ord-a1805e8461f74940b8b4b33c7b301d64
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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