1-Indanone, 4-bromo- → HCID 45112277, compound

HRID 2043011Notes

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[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH2:18][CH2:19][C:20]2=[O:25]>>[O:25]=[C:20]1[C:21]2[C:17](=[C:16]([C:2]#[C:1][C:3]3[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=3)[CH:24]=[CH:23][CH:22]=2)[CH2:18][CH2:19]1

Participants

Reactant 2

HCID 987131-Indanone, 4-bromo-

HCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 45112277HCID 45112277, compound

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (94 mg, 0.50 mmol) and 4-bromo-2,3-dihydro-1H-inden-1-one (116 mg, 0.55 mmol) according to the general procedure IF to give 110 mg (69%) of an yellow solid after purification by flash chromatography (SiO2, EtOAc:PE, 1:5): Rf=0.34 (EtOAc:PE, 1:2); 1H NMR (CDCl3) δ 7.76-7.68 (m, 2H), 7.55-7.43 (m, 2H), 7.38 (t, J=7.6 Hz, 1H), 7.22 (d, J=8.3 Hz, 2H), 3.68 (s, 1H), 3.29-3.21 (m, 2H), 2.98 (t, J=7.7 Hz, 3H), 2.77-2.71 (m, 2H), 2.65 (t, J=7.7 Hz, 2H); 13C NMR (CDCl3) δ 206.6, 173.0, 157.1, 141.5, 137.3, 136.8, 131.8 128.5, 127.5, 123.3, 122.3, 120.7, 94.8, 85.3, 51.7, 36.1, 35.3, 30.8, 25.5; ESI-MS m/z 341.1 (M+Na+).

Sources & evidence

ORD record: ord-135e17ce0d9443ed85030340c792e861
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586607B2

Reaction notes

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