(3-Bromopropyl)benzene → HCID 24995141, compound

HRID 1875361Notes

Reaction equation

[CH3:1][C:2]([C:4]1[C:9]([OH:10])=[C:8]([O:11][CH3:12])[C:7]2[O:13][CH:14]=[CH:15][C:6]=2[C:5]=1[O:16][CH3:17])=[O:3].[C:18]1([CH2:24][CH2:25][CH2:26]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:2]([C:4]1[C:9]([O:10][CH2:26][CH2:25][CH2:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:8]([O:11][CH3:12])[C:7]2[O:13][CH:14]=[CH:15][C:6]=2[C:5]=1[O:16][CH3:17])(=[O:3])[CH3:1]

Participants

Reactant 2

HCID 12503(3-Bromopropyl)benzene

HCID 68086Khellinone

Product 1

HCID 24995141HCID 24995141, compoundYield 85.8%

Procedure

Khellinone (59 mg, 0.25 mmol) and 3-(phenyl)propylbromide (46 μL, 0.30 mmol) were treated as described under General Procedure A to afford the title compound (76 mg, 85%) as a colourless solid: 1H NMR (300 MHz, CDCl3): δ 2.03 (m, 2H), 2.53 (s, 3H), 2.76 (t, J=7.8 Hz, 2H), 3.97 (s, 3H), 4.03 (s, 3H), 4.08 (t, J=6.3 Hz, 2H), 6.86 (d, J=2.4 Hz, 1H), 7.14-7.30 (m, 5H), 7.56 (d, J=2.4 Hz, 1H). MS (ES+) m/z 355.1 (M+H+).

Sources & evidence

ORD record: ord-3de7d757449c4b01a07ebd2f7cbe1de9
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309545B2

Reaction notes

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