2-Bromo-3-methylthiophene → HCID 58319095, compound

HRID 2043016Notes

Reaction equation

HRID 2043016 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][C:20]=1[CH3:21]>>[CH3:21][C:20]1[CH:19]=[CH:18][S:17][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 843142-Bromo-3-methylthiopheneHCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 58319095HCID 58319095, compound

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (95 mg, 0.50 mmol) and 2-bromo-3-methylthiophene (70 μL, 0.62 mmol) according to the general procedure IF to give 75 mg (53%) of a pale yellow solid after purification by flash chromatography (SiO2, EtOAc:PE, 1:5): Rf=0.57 (EtOAc:PE, 1:2); 1H NMR (CDCl3) δ 7.47-7.40 (m, 2H), 7.17 (dd, J=8.4, 6.7 Hz, 3H), 6.85 (d, J=5.1 Hz, 1H), 3.67 (s, 3H), 2.96 (t, J=7.7 Hz, 2H), 2.63 (t, J=7.7 Hz, 2H), 2.37 (s, 3H); 13C NMR (CDCl3) δ 173.1, 142.4, 140.8, 131.5, 129.2, 128.3, 125.7, 121.2, 118.7, 95.2, 82.0, 51.6, 35.4, 30.8, 15.0; ESI-MS m/z 307.1 (M+Na+).

Sources & evidence

ORD record
ord-e9ef39533d374703bdb82c20703897bc
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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