5-Bromo-1,2,3-trimethoxybenzene → (2-Fluoro-5-iodophenyl)(3,4,5-trimethoxyphenyl)methanone
Reaction equation
[Mg].Br[C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH3:12])=[C:5]([O:13][CH3:14])[CH:4]=1.[F:15][C:16]1[CH:24]=[CH:23][C:22]([I:25])=[CH:21][C:17]=1[C:18](Cl)=[O:19]>>[F:15][C:16]1[CH:24]=[CH:23][C:22]([I:25])=[CH:21][C:17]=1[C:18]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH3:12])=[C:5]([O:13][CH3:14])[CH:4]=1)=[O:19]Participants
Procedure
First, magnesium was added to 1-bromo-3,4,5-trimethoxybenzene as a starting material, as shown in Reaction 6, and then 2-fluoro-5-iodobenzoyl chloride was added thereto to obtain a Compound 21 derivative [(2-fluoro-5-iodophenyl)(3,4,5-trimethoxyphenyl)methanone]. Using NaOMe, the fluoro group of thus obtained compound was substituted with a methoxy group to obtain (2-methoxy-5-iodophenyl)(3,4,5-trimethoxyphenyl)methanone. Thus obtained (2-methoxy-5-iodophenyl)(3,4,5-trimethoxyphenyl)methanone (320 mg, 0.75 mmol) was dissolved in tetrahydrofuran (50 ml), and 2-(tributylstannyl)thiazole (475 mg, 1.27 mmol) and Pd(PPh3)2Cl2 (26 mg, 0.04 mmol) were slowly added thereto at room temperature. The mixture was heat refluxed for 8 hours. After completion of the reaction, the reaction mixture was extracted with water and EtOAc. The organic layer was washed with brine, and dried over anhydrous MgSO4. The solid substance was filtered off, and the filtrate was vacuum concentrated. The resulting residue was purified by column chromatography (SiO2, n-Hex/EA=1/2) to obtain Compound 583 (140 mg, 49%).
Workup
- customas shown in Reaction 6
Sources & evidence
- ORD record
- ord-8d76210923f74986aa5117910c06b0dd
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08053439B2
Reaction notes
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