KBS36-3 - Synthesis of 1-(5-phenylpyridin-2-yl)ethan-1-one (2 g)

[KlementineJBS]

Link to HIRAC and original method.

KBS36 - Synthesis of 1-(5-phenylpyridin-2-yl)ethan-1-one.docx

Reaction scheme

Need to do under nitrogen!

Outcome

1.271 g, calculated 1.2581 g to be yield, which corresponds to 99% conversion but > 100% yield (likely due to contamination with boronic acid)

[KlementineJBS]

22.08.23

1. Added the following to a flask: 2-acetyl-5-bromopyridine (1.0595 g, 5.29 mmol), phenylboronic acid (777.6 mg, 6.38 mmol, 1.2 equiv.), K2CO3 (1.4619 g, 10.58 mmol, 2 equiv.) and Pd(Ph3)4 (31.8 mg)
2. Vacuum and backfilled with N2 x 5
3. Added toluene (25 mL) and water (5 mL)
4. Left stirring at 105 C from 7.30 pm

[KlementineJBS]

23.08.23

TLC at 6 pm indicated completion. Work up as in previous attempts #114

Vial: 15.7291
Full vial: 17.0001
Mass: 1.271 g

[KlementineJBS]

H NMR

Material contained some boronic acid (approximately 20% by moles), which accounts for excess yield.

Calculated 1.2581 g to be yield, which corresponds to 99% conversion and 121% yield.

KBS36-3 cr.pdf
KBS36-3 cr_1.zip