Tin tetrachloride → (3-Methoxyphenyl)phenylacetonitrile

HRID 2046619Notes

Reaction equation

HRID 2046619 reaction equation
Cl[CH:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.C[Si]([C:21]#[N:22])(C)C.[Sn](Cl)(Cl)(Cl)Cl>C(Cl)Cl.CCCCCCC>[CH3:10][O:9][C:5]1[CH:4]=[C:3]([CH:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:21]#[N:22])[CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 24287Tin tetrachlorideHCID 82115Trimethylsilyl cyanideHCID 61083291HCID 61083291, compound

Product 1

HCID 59557385(3-Methoxyphenyl)phenylacetonitrileYield 41.7%

Reagents, catalysts & solvents 2

HCID 8900HeptaneCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(chlorophenylmethyl)-3-methoxybenzene (5.5 g, 24 mmol) in DCM (100 mL) was cooled to 0° C. Trimethylsilyl cyanide (3.5 mL, 26 mmol) was added to the stirred solution. 1.0 M of tin tetrachloride in heptane (0.75 mL, 0.75 mmol) was then added. The solution was stirred for 2 hours, then quenched with MeOH (50 mL). The solvent was removed under reduced pressure. The crude material was then purified via silica gel chromatography to obtain the title compound (2.2 g, 10 mmol).

Workup

  1. customquenched with MeOH (50 mL)
  2. customThe solvent was removed under reduced pressure
  3. customThe crude material was then purified via silica gel chromatography

Sources & evidence

ORD record
ord-a4577ff308a9445bbad658e085f0f1b8
Source dataset
uspto-grants-2013_11
Patent number
US08592453B2

Reaction notes

Loading…