Pyridiniumtribromide → 2-Bromo-1-(3-methyl-4'-nitro-1,1'-biphenyl-4-yl)ethanone

HRID 9559

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[C:8](=[O:10])[CH3:9].[Br-:20].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(O)(=O)C>[Br:20][CH2:9][C:8]([C:7]1[CH:6]=[CH:5][C:4]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[CH:3][C:2]=1[CH3:1])=[O:10]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 1-(3-methyl-4′-nitro-1,1′-biphenyl-4-yl)ethanone (5.66 g, 22 mmol), pyridinium tribromide (10.63 g, 33.0 mmol), and glacial acetic acid (60 mL) was stirred at 110° C. for 3 h. The reaction mixture was cooled to 0–5° C., and the precipitated product was collected by filtration and washed with small amounts of water, ethanol, and diethyl ether. The crude material was purified by flash chromatography (5:95 ethyl acetate/hexane) to give 2-bromo-1-(3-methyl-4′-nitro-1,1′-biphenyl-4-yl)ethanone as a light yellow solid (4.33 g, 59% yield). HPLC ret. time 3.63 min; 1H NMR (CDCl3) δ: 2.63 (s, 3H), 2.25 (s, 2H), 7.52–7.58 (m, 2H), 7.72–7.83 (m, 3H), 8.32 (d, 2H).

Workup

temperatureThe reaction mixture was cooled to 0–5° C.
filtrationthe precipitated product was collected by filtration
washwashed with small amounts of water, ethanol, and diethyl ether
customThe crude material was purified by flash chromatography (5:95 ethyl acetate/hexane)

Sources & evidence

ORD record: ord-1babce0031024287921edca41706873d
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091228B2

Linked notes

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