Hydrochloric Acid → 2-Cyano-4'-methylbiphenyl

HRID 1937097Notes

Reaction equation

HRID 1937097 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl>Cl[Pd]Cl.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:3]1([CH3:4])[CH:6]=[CH:7][C:8]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[C:4]#[N:5])=[CH:9][CH:2]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 162722-Bromobenzonitrile

Product 1

HCID 1455122-Cyano-4'-methylbiphenylYield 96%

Reagents, catalysts & solvents 1

HCID 11017392(1,3-Bis(diphenylphosphino)propane)palladium(II) chlorideCatalyst

Procedure

PdCl2/dppp (0.023 g, 1 mol %) is added and then o-bromobenzonitrile (0.72 g, 3.955 mmol) is added. The temperature rises from +10 to +300° C. over 15 min and then slowly falls to +250° C. After stirring for 3 hours at room temperature, the reaction mixture is hydrolysed using a 1N hydrochloric acid solution (15 ml). After extracting with ethyl ether, the organic phase is dried over potassium carbonate, filtered and then evaporated under vacuum. The oil thus formed is subsequently purified by chromatography (silica: 20 g; eluant: petroleum ether/ethyl acetate=95/5). The o-(p-tolyl)benzonitrile thus obtained is then harvested, with a yield of 96%, in the form of off-white crystals.

Workup

  1. customslowly falls to +250° C
  2. extractionAfter extracting with ethyl ether
  3. dry with materialthe organic phase is dried over potassium carbonate
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customThe oil thus formed
  7. customis subsequently purified by chromatography (silica: 20 g; eluant: petroleum ether/ethyl acetate=95/5)

Sources & evidence

ORD record
ord-04a9841fca0a44d4940ce23726be87c6
Source dataset
uspto-grants-2002_05
Patent number
US06392080B1

Reaction notes

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