2-Iodophenylacetonitrile → Methyl 3-(4-((2-(cyanomethyl)phenyl)ethynyl)phenyl)propanoate

HRID 2042997Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1)#[CH:2].I[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][C:23]#[N:24]>>[C:23]([CH2:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:2]#[C:1][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1)#[N:24]

Participants

Reactant 2

HCID 44022822-Iodophenylacetonitrile

HCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 67072780Methyl 3-(4-((2-(cyanomethyl)phenyl)ethynyl)phenyl)propanoate

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (74 mg, 0.39 mmol) and 2-(2-iodophenyl)acetonitrile (60 μL, 0.43 mmol) according to the general procedure IC to give 74 mg (62%) of an orange solid after purification by flash chromatography (SiO2, EtOAc:PE, 1:4). Rf=0.08 (EtOAc:PE, 1:4); 1H NMR (CDCl3) δ 7.55-7.46 (m, 4H), 7.37-7.34 (m, 2H), 7.21 (d, J=8.4 Hz, 2H), 3.96 (s, 2H), 3.67 (s, 3H), 2.97 (t, J=7.7 Hz, 2H), 2.64 (t, J=7.5 Hz, 2H); 13C NMR (CDCl3) δ 173.0, 141.6, 132.3, 131.7, 131.6, 128.9, 128.5, 128.1, 122.9, 120.4, 117.4, 95.6, 85.7, 51.7, 35.3, 30.8, 22.7; ESI-MS m/z 326.1 (M+Na+).

Sources & evidence

ORD record: ord-74510ed810d84f1b8e1ab938d4a21493
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586607B2

Reaction notes

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