3-Bromobenzaldehyde CAS 3132-99-8 | 821696
4-(Prryolidin-1-yl)benzaldehyde is known to be synthesised via Buchwald-Hartwig coupling using Pd20(dba)3 catalyst and para-Bromobenzaldehyde in literature. The aim of this experiment was to imitate the reaction  but employ meta-Bromobenzaldehyde and reflux at a higher temperature; in order to compensate the slow rate of from the aldehyde group (i.e meta-directing) to yield the corresponding meta-counterpart 3-(Prryolidin-1-yl)benzaldehyde.
3132-99-8 - 3-Bromobenzaldehyde, 97% - A11941 - Alfa …
Into a dry 250mL round bottom flask was first charged 3-Bromobenzaldehyde (1.25, 6.75mmol), Ethylene glycol (2.10mL, 33.75mmol), Toluene (30mL) and lastly TsOH.H2O (0.093mg, 0.54mmol). A Dean-stark apparatus was set up as shown (below) prior preparing mixture. Aluminium foil and cotton wool covered the distillation trap component; the side-arm (burette component) was filled with Toluene. Water flow was switched on allowing a reflux to occur at 120-150 oC induced by an electrical hot plate.
The set-up as a whole would allow the reaction vapour (toluene and water) to travel up and cool into the Burette component. Toluene is less dense than water so an immiscible bottom layer of water was expected. Overnight, distilled mixture was cloudy indicating a successful azeotrope but minimal amount of water being produced during the reaction.
Smoliar NIa. Determination of 3-bromobenzaldehyde, 3-phenoxybenzaldehyde and 3-phenoxybenzyl alcohol in the air of the work place.Gig Sanit.1990,2(69).
3 bromobenzaldehyde synthesis essay - Door Tech LLC
After an unsuccessful attempt in cross-coupling the starting aldehyde and amine (ID-1-001), a protection synthesis was attempted to protect the aldehyde of meta-Bromobenzaldehyde in a form of a 1,3-dioxolane. The resulting product is known to offer more stability  to the aldehyde hence the Buchwald-Hartiwg coupling should be more liable between the Pyrrolidine and protected Bromobenzaldehyde.
Into a dry 250mL round bottom flask was first charged 3-Bromobenzaldehyde (3.17mL, 10.8mmol), Ethylene glycol (3.00mL, 54mmol), Toluene (40mL) and lastly TsOH.H2O (0.093mg, 0.54mmol). A reflux was set up for the reaction using a Leibig condenser. The RBF was clamped above a hot plate inducing stirring and heating around 200 oC.
3-Bromobenzaldehyde CAS#: 3132-99-8 - ChemicalBook
In a 50mL round bottom flask was first charged 3-Bromobenzaldehyde (0.126mL, 1.08mmol), dry Toluene solvent (2.5mL), then Pyrrolidine (0.088mL, 1.08mL), BINAP (0.0268g, 0.0432mmol), NaO-tBu (0.156g, 1.62mmol) and lastly Pd(dba)2 (0.0196g, 0.0216mL) while being stirred and maintained under Nitrogen. Reaction mixture was degassed for 15 minutes prior increasing temperature to 100-110 oC from an electrical hot plate. A yellow-red brown colour was observed from 1 to 3 hours of the reaction.