3-Bromo-o-xylene → Methyl 3-(4-((2,3-dimethylphenyl)ethynyl)phenyl)propanoate

HRID 2042984Notes

Reaction equation

HRID 2042984 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[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:17]=1[CH3:23]>>[CH3:23][C:17]1[C:18]([CH3:22])=[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

Participants

3

Reactant 2

HCID 684723-Bromo-o-xyleneHCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 58319124Methyl 3-(4-((2,3-dimethylphenyl)ethynyl)phenyl)propanoate

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (99 mg, 0.53 mmol) and 1-bromo-2,3-dimethylbenzene (0.08 mL, 0.59 mmol) according to the general procedure IC to give 22 mg (14%) of an orange oil after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:5). Rf: 0.42 (EtOAc:hexanes, 2:5); 1HNMR (CDCl3) δ 7.47-7.44 (m, 2H), 7.37-7.34 (m, 1H), 7.19-7.17 (m, 2H), 7.12-7.03 (m, 2H), 3.67 (s, 3H), 2.99-2.94 (t, 2H, J=7.8 Hz), 2.66-2.61 (t, 2H, J=7.8 Hz), 2.45 (s, 3H), 2.29 (s, 3H); 13CNMR (CDCl3) δ 173.7, 142.7, 137.8, 132.2, 130.8, 130.5, 129.6, 126.4, 124.0, 122.1, 93.5, 89.2, 35.6, 31.4, 20.3, 17.6; ESI-MS m/z 315.1 (MNa+).

Sources & evidence

ORD record
ord-4aaafd4a7241417786fd93e5390498a7
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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