Triphenylphosphine → HCID 23297134, compound

HRID 1954486Notes

Reaction equation

HRID 1954486 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[Mg]Br.Br[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([CH3:20])[CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.[Pd](Cl)Cl>[CH3:20][C:14]1[CH:13]=[C:12]([C:3]2[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=2[CH3:1])[CH:19]=[CH:18][C:15]=1[C:16]#[N:17]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 1442674-Bromo-2-methylbenzonitrileHCID 178425073HCID 178425073, compound

Product 1

HCID 23297134HCID 23297134, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

2,5-dimethylphenylmagnesium bromide (84 g, 20% solution in tetrahydrofuran) is added dropwise over five hours to a refluxing solution of 4-bromo-2-methylbenzonitrile (16 g), palladium (II) chloride (0.57 g) and triphenylphosphine (1.7 g) in tetrahydrofuran (100 ml). [HPLC: yield 90-95%]. After cooling to room temperature tetrahydrofuran is removed under vacuum. The residue is taken up in toluene/water (1:1) (200 ml) and filtered. The aqueous phase is separated off, and the solvent removed by distillation. The crude product is recrystallised from ethanol to give 3,2',5'-trimethylbiphenyl-4-carbonitrile as a solid, m.pt. 96-97° C. 1H NMR (CDCl3): 2.19(s,3H), 2.34(s,3H), 2.58(s,3H), 6.99(s,1H), 7.08-7.25(m,3H), 7.62(d,1H).

Workup

  1. customis removed under vacuum
  2. filtrationfiltered
  3. customThe aqueous phase is separated off
  4. customthe solvent removed by distillation
  5. customThe crude product is recrystallised from ethanol

Sources & evidence

ORD record
ord-9559027ad4b948bb80b02c000568ba45
Source dataset
uspto-grants-2000_09
Patent number
US06121480

Reaction notes

Loading…