2-Iodotoluene → Methyl 3-(4-(o-tolylethynyl)phenyl)propanoate

HRID 2042977Notes

Reaction equation

HRID 2042977 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]=[CH:18][C:17]=1[CH3:22]>>[C:17]1([CH3:22])[CH:18]=[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 51282-IodotolueneHCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 45113002Methyl 3-(4-(o-tolylethynyl)phenyl)propanoate

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (90 mg, 0.48 mmol) and iodo-2-methylbenzene (0.07 mL, 0.55 mmol) according to the general procedure IB to give 36 mg (31%) of an orange oil after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:30→1:10). Rf: 0.27 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 7.49-7.44 (m, 3H), 7.23-7.17 (m, 5H), 3.67 (s, 3H), 2.99-2.94 (t, 2H, J=7.8 Hz), 2.66-2.61 (t, 2H, J=7.8 Hz), 2.50 (s, 3H); 13CNMR (CDCl3) δ 173.1, 140.8, 140.1, 131.8, 131.6, 129.4, 128.3, 128.2, 125.5, 123.1, 121.5, 93.2, 88.1, 51.6, 35.4, 30.8, 20.7; ESI-MS m/z 301.1 (MNa+).

Sources & evidence

ORD record
ord-71d74590cd9b4d1081eb27b602782040
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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