1-Iodo-3,5-dimethylbenzene → HCID 58319093, compound

HRID 2042983Notes

Reaction equation

HRID 2042983 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]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=1>>[CH3:23][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]=[C:20]([CH3:22])[CH:19]=1

Participants

3

Reactant 2

HCID 1409241-Iodo-3,5-dimethylbenzeneHCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 58319093HCID 58319093, compound

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (99 mg, 0.53 mmol) and 1-iodo-3,5-dimethylbenzene (0.08 mL, 0.55 mmol) according to the general procedure IC to give 128 mg (83%) of an orange solid after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:5). Rf: 0.59 (EtOAc:hexanes, 2:5); 1HNMR (CDCl3) δ 7.21-7.19 (m, 2H), 7.07-7.05 (m, 2H), 6.90-6.89 (m, 2H), 6.78-6.77 (m, 1H), 2.72-2.67 (t, 2H, J=7.8 Hz), 2.42-2.37 (t, 2H, J=7.8 Hz), 2.05 (s, 6H); 13CNMR (CDCl3) δ 173.1, 140.7, 137.8, 131.7, 130.1, 129.2, 128.3, 122.9, 121.4, 89.4, 88.6, 51.6, 35.4, 30.8, 21.1; ESI-MS m/z 315.1 (MNa+).

Sources & evidence

ORD record
ord-204e5f237ae040848e65c2bb4475c180
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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