search

KlementineJBS / USYD_PhD_ELN

This repository forms the electronic laboratory notebook (ELN)for Klementine Burrell-Sander's PhD's
2 stars 0 forks source link

KBS42-1 - NBS reaction on 2-acetyl-4-chloropyridine #123

Closed KlementineJBS closed 9 months ago

KlementineJBS commented 11 months ago

Link to HIRAC.

HIRAC NBS reaction Breaking Good.docx

Reaction scheme

Image

Outcome

320.4 mg of which 267.2 mg = product (83% conversion, so 71% yield)

KlementineJBS commented 11 months ago
  1. Dissolved SM (248.6 mg, 1.60 mmol) in MeCN (50 mL)
  2. Added tosic acid (430 mg, 2.50 mmol, 1.6 equiv.) and NBS (341 mg, 1.92 mmol, 1.2 equiv.)
  3. Left stirring at 85 C from 4.15 pm
KlementineJBS commented 11 months ago

TLC indicated reaction was not yet complete but worked up anyway.

  1. Rotovapped off MeCN
  2. Dissolved in 25 mL DCM
  3. Washed with water (2 x 25 mL) and brine (25 mL)
  4. Dried over mag sulphate and rotovapped down

Vial: 15.7187 Full vial: 16.0391 Mass: 320.4 mg (83% conversion, 71% yield)

KlementineJBS commented 11 months ago

H NMR

Assume that 2.70 is starting material methyl peak. Unsure exactly which peak is the methylene in the product.

KBS42-1 cr.pdf 2-acetyl-4-chloropyridine_1.zip KBS42-1 cr_1.zip