1-Iodo-3-nitrobenzene → Methyl 3-(4-((3-nitrophenyl)ethynyl)phenyl)propanoate

HRID 2042980Notes

Reaction equation

HRID 2042980 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]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=1>>[N+:22]([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:21]=[CH:20][CH:19]=1)([O-:24])=[O:23]

Participants

3

Reactant 2

HCID 125741-Iodo-3-nitrobenzeneHCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 58319122Methyl 3-(4-((3-nitrophenyl)ethynyl)phenyl)propanoate

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (102 mg, 0.54 mmol) and 1-iodo-3-nitrobenzene (146 mg, 0.58 mmol) according to the general procedure IC to give 113 mg (67%) of a pale orange solid after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:5). Rf: 0.30 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 8.36-8.35 (m, 1H), 8.18-8.14 (m, 1H), 7.82-7.79 (m, 1H), 7.55-7.46 (m, 3H), 7.23-7.20 (m, 2H), 3.68 (s, 3H), 3.01-2.96 (t, 2H, J=7.8 Hz), 2.68-2.62 (t, 2H, J=7.8 Hz); 13CNMR (CDCl3): δ 173.0, 148.2, 141.8, 137.1, 131.9, 129.3, 128.5, 126.3, 125.2, 122.8, 120.1, 91.9, 86.6, 51.7, 35.3, 30.8; EI-MS m/z 309 (M+).

Sources & evidence

ORD record
ord-6bf0b606ee0b4e7f97e8039fa8ff277e
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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