Nitrogen → [1,1'-Biphenyl]-3,3,5-tricarbaldehyde

HRID 58997Notes

Reaction equation

HRID 58997 reaction equation
[CH:1]1[C:6]([CH:7]=[O:8])=[CH:5][C:4](Br)=[CH:3][C:2]=1[CH:10]=[O:11].C([C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1)=O.[C:23](=O)([O-])[O-:24].[K+].[K+].N#N>COCCOC.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:4]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:3][C:2]([CH:23]=[O:24])([CH:10]=[O:11])[CH:1]=[C:6]([CH:7]=[O:8])[CH:5]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 27343563-Formylphenylboronic acidHCID 143832305-Bromobenzene-1,3-dicarbaldehyde

Product 1

HCID 117844897[1,1'-Biphenyl]-3,3,5-tricarbaldehydeYield 62%

Reagents, catalysts & solvents 2

HCID 11776TriphenylphosphineCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 5-bromoisophthaldehyde (2.13 g, 10.0 mmol), 3-formylphenylboronic acid (1.49 g, 10.0 mmol) and potassium carbonate (2.76 g, 20.0 mmol) in DME/H2O (5:1 50 mL) was purged with N2 for 5 min. Tetrakispalladium triphenylphosphine (0.12 g, 0.1 mmol) was added and the reaction mixture was heated to 90° C. and stirred for 16 h. The reaction mixture was cooled, filtered through a pad of Celite diatomaceous earth and the solvent evaporated under reduced pressure. Purification by column chromatography (10% EtOAc/hexanes) afforded the desired product (1.47 g, 62%) as a tan solid. 1H NMR (300 MHz, CDCl3) δ ppm 10.20 (s, 2H), 10.10 (s, 1H), 8.42 (s, 3H), 8.21 (s, 1H), 7.98 (t, J=5.4 Hz, 2H), 7.72 (t, J=5.4 Hz, 2H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through a pad of Celite diatomaceous earth
  3. customthe solvent evaporated under reduced pressure
  4. customPurification by column chromatography (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2f7219d827784ab18585eb03f691ab87
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

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