Sodium Carbonate → 3,5-Bis[3',5'-bis(3'',5-''-di-t-butylstyryl)styryl]benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,5-dibromobenzaldehyde (8.21 g, 31.1 mmoles), 3,5-bis(3′,5′-di-t-butylstyryl)styrene (41.4 g, 77.7 mmoles), anhydrous sodium carbonate (6.59 g, 62.2 mmoles), trans-di(μ-acetato)-bis[o-(di-o-tolylphosphino)benzyl]dipalladium (II) (58.3 mg, 0.062 mmoles, 0.1 mole %), 2,6-di-t-butylcresol (1.71 g, 7.77 mmoles) and anhydrous N,N-dimethylacetamide (100 mL) was degassed extremely thoroughly whilst stirring under oil-pump vacuum, purging with argon. The reaction mixture was then heated under argon at 130° C. for 17 hours. After further addition of anhydrous N,N-dimethylacetamide (100 mL), the reaction mixture was degassed for a second time and then heated at 130° C. for a further 5.5 hours. Further anhydrous N,N-dimethylacetamide (100 mL) was then added and the reaction was continued for a further 1 hour. The resulting sludge was washed with distilled water (3×250 mL) and dissolved in dichloromethane (1500 mL). The organic fraction was washed with distilled water (500 mL), dried over anhydrous sodium sulphate and evaporated to give a cream solid. The crude product was recrystallized from dichloromethane/pet. ether (60-80) three times before chromatography on flash silica using chloroform-pet.ether (60-80) (2:3) as the eluent gave a white solid of 3,5-bis[3′,5′-bis(3″,5-″-di-t-butylstyryl)styryl]benzaldehyde (25.2 g, 69%); δH(500 MHz; CDCl1) 1.41 (72H, s, t-Bu), 7.20 and 7.32 (8H, d, J 16, G-2 vinyl H), 7.34 and 7.38 (4H, d, J 16.5, G-1 vinyl H), 7.42 (4H, dd, J 2, sp H), 7.46 (8H, d, J 2, sp H), 7.67 (4H, s, G-1 bp H), 7.69 (2H, s, G-1 bp H), 8.00 (3H, s, cp H) and 10.14 (1H, s, CHO) which is identical to that reported.

Provenance & Evidence