KBS42-3 - NBS reaction on 2-acetyl-4-chloropyridine (1 g scale)

[KlementineJBS]

Link to HIRAC.

HIRAC NBS reaction Breaking Good.docx

Reaction scheme

Outcome

1.2029 g (of which 570 mg was product, for 47% conversion and 46% yield)

[KlementineJBS]

1. Dissolved SM (829.1 mg, 5.33 mmol) in MeCN (175 mL)
2. Added tosic acid (1.3762 g, 8.00 mmol, 1.5 equiv.) and NBS (1.1497 g, 6.46 mmol, 1.2 equiv.)
3. Left stirring at 65 C from 2.45 pm

[KlementineJBS]

TLC indicated SM remained but worked up anyway.

See #132 for workup. Used 150 mL DCM, 2 x 100 mL water, 100 mL brine.

Empty vial: 15.6664 Full vial: 16.8693 Mass: 1.2029 g (of which 570 mg was product, for 47% conversion and 46% yield)

[KlementineJBS]

H NMR

Inconclusive. Still not exactly sure which peak is the methylene - will run a C NMR to try and find out.

KBS42-3 cr.pdf KBS42-3 cr_1.zip