Benzene, 1-iodo-3-(trifluoromethyl)- → HCID 67072522, compound

HRID 2042982Notes

Reaction equation

HRID 2042982 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]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1>>[F:23][C:22]([F:25])([F:24])[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]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 67868Benzene, 1-iodo-3-(trifluoromethyl)-HCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 67072522HCID 67072522, compound

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (101 mg, 0.54 mmol) and 1-iodo-3-(trifluoromethyl)benzene (0.09 mL, 0.62 mmol) according to the general procedure IC to give 119 mg (67%) of an yellow oil after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:5). Rf: 0.58 (EtOAc:hexanes, 2:5); 1HNMR (CDCl3) δ 7.77 (s, 1H), 7.68-7.66 (m, 1H), 7.57-7.55 (m, 1H), 7.48-7.43 (m, 3H), 7.21-7.18 (m, 2H), 3.67 (s, 3H), 3.00-2.94 (t, 2H, J=7.8 Hz), 2.67-2.61 (t, 2H, J=7.8 Hz); 13CNMR (CDCl3) δ 173.0, 141.4, 134.6, 131.8, 128.8, 128.4, 128.3, 128.3, 124.7, 124.6, 124.6, 124.3, 120.5, 90.8, 87.5, 51.6, 35.3, 30.8; ESI-MS m/z 355.1 (MNa+).

Sources & evidence

ORD record
ord-653454833ac1483c8a2d58d7c297ddf9
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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