3-Iodobenzonitrile → HCID 67072629, compound

HRID 2042979Notes

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

Participants

Reactant 2

HCID 1443413-Iodobenzonitrile

HCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 67072629HCID 67072629, compound

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (103 mg, 0.55 mmol) and 3-iodobenzonitrile (134 mg, 0.59 mmol) according to the general procedure IC to give 68 mg (58%) of an orange-brown solid after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:5). Rf: 0.26 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 7.79-7.78 (m, 1H), 7.73-7.70 (m, 1H), 7.61-7.57 (m, 1H), 7.48-7.43 (m, 3H), 7.22-7.18 (m, 2H), 3.67 (s, 3H), 3.00-2.95 (t, 2H, J=7.8 Hz), 2.67-2.62 (t, 2H, J=7.8 Hz); 13CNMR (CDCl3) δ 173.0, 141.7, 135.5, 134.8, 131.9, 131.3, 129.2, 128.5, 125.0, 120.2, 118.1, 116.7, 112.8, 91.7, 86.6, 51.7, 35.3, 30.8; EI-MS m/z 289 (M+).

Sources & evidence

ORD record: ord-336faf0e74d6464cbc6f3fd08ca697cd
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586607B2

Reaction notes

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