Water → 2-(4-Methoxyphenyl)benzonitrile

HRID 1954483

Reaction equation

HRID 1954483 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Mg]Br)=[CH:5][CH:4]=1.Br[C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1.[Pd](Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:12]2[C:13]([C:14]#[N:15])=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 162722-BromobenzonitrileHCID 178491912HCID 178491912, compound

Product 1

HCID 13933732-(4-Methoxyphenyl)benzonitrileYield 94%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

4-methoxyphenylmagnesium bromide (280 g, 15% solution in tetrahydrofuran) is added dropwise over seven hours to a refluxing solution of 2-bromobenzonitrile (32 g), palladium (II) chloride (1.3 g) and triphenylphosphine (3.8 g) in tetrahydrofuran (210 ml). [HPLC: yield 94-95%]. After cooling to room temperature and the addition of water (50 ml), tetrahydrofuran is removed under vacuum. The residue is extracted with toluene (230 ml). Insoluble material is filtered off and the solvent distilled off. The crude product is recrystallised from ethanol to give 4'-methoxybiphenyl-2-carbonitrile as a solid, m.pt. 82-83° C. 1H NMR (CDCl3): 3.90(s,3H), 7.02(d,2H), 7.36-7.52(m,4H), 7.59-7.65(m,1H), 7.74(d,1H).

Workup

  1. customis removed under vacuum
  2. extractionThe residue is extracted with toluene (230 ml)
  3. filtrationInsoluble material is filtered off
  4. distillationthe solvent distilled off
  5. customThe crude product is recrystallised from ethanol

Sources & evidence

ORD record
ord-4748a8aea93e43cfbe529d93cc49aef3
Source dataset
uspto-grants-2000_09
Patent number
US06121480

Linked notes

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