[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])([O-:3])=[O:2].[CH3:13][Si:14]([CH3:22])([CH3:21])[C:15]#[C:16][Si](C)(C)C.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](=[O:7])[C:16]#[C:15][Si:14]([CH3:22])([CH3:21])[CH3:13])([O-:3])=[O:2]A solution of 2-nitrobenzoyl chloride (13) (225 g; 1.2 moles) and 1,2-bis(trimethylsilyl)ethyne (205 g; 1.2 moles) in dichloromethane (3 L) was cooled to 0° C. Aluminum chloride (159.2 gram, 1.2 moles) was slowly added at 0° C. over 10 minutes while keeping the internal reaction temperature below 10° C. After the addition, the reaction mixture was stirred at 5-10° C. for 1 hour. With stirring, the black reaction mixture was poured into ice-water mixture (2 kg of ice and 1 kg of water). The resulting suspension was filtered and the filter cake was washed with dichloromethane (200 mL). The organic phase of the combined filtrate was separated. The aqueous phase was extracted 2-times with dichloromethane (2×2 L). The combined organic phase was washed with water (2 L), filtered through a Celite pad (200 g), dried over sodium sulfate (120 g), and concentrated at the temperature below 30° C. (bath temperature) to dryness to give 294 g (99% yield) of the desired product in 95% HPLC purity.
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