2-Bromothiophene → HCID 45112278, compound

HRID 2043015Notes

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[S:17][CH:18]=[CH:19][CH:20]=1>>[S:17]1[CH:18]=[CH:19][CH:20]=[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

Reactant 2

HCID 138512-Bromothiophene

HCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 45112278HCID 45112278, compound

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (95 mg, 0.50 mmol) and 2-bromothiophene (60 μL, 0.62 mmol) according to the general procedure IF to give 97 mg (71%) of a white solid after purification by flash chromatography (SiO2, EtOAc:PE, 1:5): Rf=0.44 (EtOAc:PE, 1:2); 1H NMR (CDCl3) δ 7.50-7.39 (m, 2H), 7.31-7.23 (m, 2H), 7.18 (d, J=8.4 Hz, 2H), 7.00 (dd, J=5.1, 3.7 Hz, 1H), 3.67 (s, 3H), 2.96 (t, J=7.7 Hz, 2H), 2.63 (t, J=7.7 Hz, 2H); 13C NMR (CDCl3) δ 173.1, 141.1, 131.8, 131.6, 128.4, 127.1, 127.1, 123.4, 120.9, 92.9, 82.3, 51.6, 35.3, 30.8; ESI-MS m/z 293.1 (M+Na+).

Sources & evidence

ORD record: ord-f1b8e941282a4ee989f93a37af270529
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586607B2

Reaction notes

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