Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[CH2:9]([Li])[CH2:10][CH2:11][CH3:12].[C:14](Cl)(=[O:24])[C:15]1[CH:23]=[CH:22][CH:21]=[C:17]([C:18](Cl)=[O:19])[CH:16]=1.O1C[CH2:29][CH2:28][CH2:27]1>>[CH3:12][C:11]1[CH:27]=[C:28]([CH:29]=[CH:9][CH:10]=1)[C:14]([C:15]1[CH:23]=[CH:22][CH:21]=[C:17]([C:18](=[O:19])[C:6]2[CH:7]=[CH:2][CH:3]=[C:4]([CH3:8])[CH:5]=2)[CH:16]=1)=[O:24]Participants
Conditions
- Temperature
- -78 °C
Procedure
3-bromotoluene (6.684 g, 39.08 mmol) was dissolved in anhydrous tetrahydrofuran (30 mL) under an inert atmosphere of nitrogen. The solution was stirred for 5 min and cooled to −78° C. followed by the dropwise addition of n-butyllithium in hexanes (2.5M; 13.6 mL). After stirring for 3.5 h, the Weinreb amide of isophthaloyl dichloride was added dropwise and the solution was stirred for 1 h at −78° C. The reaction mixture was quenched with 1 M HCl (40 mL) and the products were extracted with dichloromethane (2×50 mL). The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. Purification using flash chromatography (silica gel, hexanes:ethyl acetate, gradient, 95:5 to 70:30) afforded 2.465 g, 9.77 mmol) 1-(3-methylbenzoyl),3-(3-methylbenzoyl)benzene 8 in a 72% yield.
Workup
- stirringAfter stirring for 3.5 h
- stirringthe solution was stirred for 1 h at −78° C
- customThe reaction mixture was quenched with 1 M HCl (40 mL)
- extractionthe products were extracted with dichloromethane (2×50 mL)
- washThe combined organic phases were washed with brine
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was removed under reduced pressure
- customPurification
Sources & evidence
- ORD record
- ord-7d242060510142afa59ea4798863c9ef
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877967B2
Linked notes
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