1-Bromo-2-iodobenzene → HCID 45112279, compound

HRID 2043010Notes

Reaction equation

HRID 2043010 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].[Br:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1I>>[Br:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=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

Participants

3

Reactant 2

HCID 114151-Bromo-2-iodobenzeneHCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 45112279HCID 45112279, compound

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (300 mg, 1.59 mmol) and 1-bromo-2-iodobenzene (0.3 mL, 2.34 mmol) according to the general procedure ID to give 340 mg (62%) of an yellow oily product after purification by flash chromatography (SiO2, EtOAc:PE, 1:5). Rf=0.27 (EtOAc:PE, 1:5); 1H NMR (CDCl3) δ 7.61 (dd, J=8.0, 1.1 Hz, 1H), 7.54 (dd, J=7.7, 1.7 Hz, 1H), 7.52-7.48 (m, 2H), 7.28 (td, J=7.6, 1.2 Hz, 1H), 7.22-7.14 (m, 3H), 3.67 (s, 3H), 2.97 (t, J=7.7 Hz, 2H), 2.64 (t, J=7.7 Hz, 2H); 13C NMR (CDCl3) δ 173.1, 141.3, 133.2, 132.4, 131.8, 129.3, 128.4, 127.0, 125.6, 125.5, 120.9, 93.9, 87.8, 51.7, 35.4, 30.9; ESI-MS m/z 365.0 (M+Na+).

Sources & evidence

ORD record
ord-866d898113fe4705837163ed9ce6ea88
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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