Dimethyl Sulfoxide → 5-Bromo-2-[2-(3-methoxy-2-methyl-phenyl)-ethyl]-phenylacetonitrile

HRID 730176Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[C:13]=2[CH3:20])=[C:6]([CH2:8]I)[CH:7]=1.CS(C)=O.[C-:25]#[N:26].[K+]>ClCCl.C(O)(C)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[C:13]=2[CH3:20])=[C:6]([CH2:8][C:25]#[N:26])[CH:7]=1

Participants

Conditions

Temperature: 42 °C

Procedure

To 5-bromo-2-[2-(3-methoxy-2-methylphenyl)-ethyl]-phenyliodomethane 9 (5.56 g; 12.5 mmol) in dichloromethane (10 mL), isopropyl alcohol (10 mL), and DMSO (3 mL), was added potassium cyanide (1.22 g; 18.8 mmol). The mixture was stirred at 42° C. for 16.5 hours and concentrated in vacuo. The resultant residue was taken up in dichloromethane and water. The solution was shaken and the layers were separated. The organic layer was washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo to give an amber oil. The oil was chromatographed using SiO2 and hexane/ethyl acetate (3:2) as eluent to give compound 10, 1.99 g; 46% yield.

Workup

concentrationconcentrated in vacuo
stirringThe solution was shaken
customthe layers were separated
washThe organic layer was washed sequentially with water and brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customto give an amber oil
customThe oil was chromatographed

Sources & evidence

ORD record: ord-adf4743ca3f840c3ac798207ed6bb67e
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582667B2

Reaction notes

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