4-Iodotoluene → Methyl 3-(4-(p-tolylethynyl)phenyl)propanoate

HRID 2042978Notes

Reaction equation

HRID 2042978 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][C:19]([CH3:22])=[CH:18][CH:17]=1>>[C:19]1([CH3:22])[CH:20]=[CH:21][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:17][CH:18]=1

Participants

3

Reactant 2

HCID 122074-IodotolueneHCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 58319083Methyl 3-(4-(p-tolylethynyl)phenyl)propanoate

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (90 mg, 0.48 mmol) and iodo-4-methylbenzene (0.07 mL, 0.55 mmol) according to the general procedure IB to give 18 mg (15%) of an orange oil after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:30→1:10). Rf: 0.42 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 7.45-7.39 (m, 4H), 7.18-7.13 (m, 4H), 3.67 (s, 3H), 2.98-2.93 (t, 2H, J=7.8 Hz), 2.66-2.60 (t, 2H, J=7.8 Hz), 2.36 (s, 3H); 13CNMR (CDCl3) δ 173.1, 140.6, 138.3, 131.7, 131.4, 129.1, 128.3, 121.4, 120.2, 89.3, 88.6, 51.6, 35.4, 30.8, 21.5; EI-MS m/z 278 (M+).

Sources & evidence

ORD record
ord-d3d6865e84cb4caba5d790692af7986b
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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