Dimethylformamide → Biphenyl

HRID 600106Notes

Reaction equation

HRID 600106 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.CN(C=O)C>C1(C)C=CC=CC=1.[Cu]>[C:3]1([C:4]2[CH:8]=[CH:9][CH:2]=[CH:3][CH:4]=2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:2]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 811292-Bromobenzaldehyde

Product 1

HCID 7095BiphenylYield 50%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1140TolueneSolvent

Procedure

2-bromo benzaldehyde (266 g, 1.35 mol) was heated to 185° C. and then copper powder (201.16 g, 3.17 mmol) was added portion wise to the liquid. After 30 mins, DMF (100 mL) was added to the solution and heating maintained for a further 8 h. After cooling to room temperature the product was dissolved in toluene and filtered through celite. Purification via column chromatography eluting with Hexane:EtOAc (6:1) gave a foam. Recrystallisation from Et2O/hexane gave 73.27 g (50% yield); 1H NMR (CDCl3) 9.81 (2H, s), 8.04 (2H, d, J 7.6), 7.65 (2H, dt, J 1.2, 7.2), 7.58 (2H, t, J 7.2), 7.34 (2H, d, J 7.6); 13C NMR 114.05, 119.97, 121.68, 123.54, 140.54.

Workup

  1. temperatureheating
  2. temperaturemaintained for a further 8 h
  3. filtrationfiltered through celite
  4. customPurification via column chromatography
  5. washeluting with Hexane:EtOAc (6:1)
  6. customgave a foam
  7. customRecrystallisation from Et2O/hexane
  8. customgave 73.27 g (50% yield)

Sources & evidence

ORD record
ord-42ccc2a4b94a4d8ca4f04a3214a67d7b
Source dataset
uspto-grants-2011_03
Patent number
US07898163B2

Reaction notes

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