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KlementineJBS / USYD_PhD_ELN

This repository forms the electronic laboratory notebook (ELN)for Klementine Burrell-Sander's PhD's
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KBS40-2 - NBS reaction on 2-acetyl-5-bromopyridine (1 g scale) #126

Closed KlementineJBS closed 9 months ago

KlementineJBS commented 10 months ago

Link to HIRAC.

HIRAC NBS reaction Breaking Good.docx

Reaction scheme

KBS40 NBS reaction on 2-acetyl-5-bromopyridine

Outcome

1.5429 g, of which 1534 g is calculated to be mono or di bromo product. 99% conversion rate and 94% yield.

KlementineJBS commented 10 months ago

10.08.23

  1. Dissolved SM (1.0207 g, 5.09 mmol) in MeCN (200 mL)
  2. Added tosic acid (1.4489 g, 8.41 mmol, 1.7 equiv.) and NBS (1.0925 g, 6.14 mmol, 1.2 equiv.)
  3. Heated to 85 C with stirring from 3.30 pm
KlementineJBS commented 10 months ago

11.08.23

  1. Added extra tosic acid (740 mg) and NBS (494 mg).
KlementineJBS commented 10 months ago

TLC indicated that SM remained, but worked up anyway. Reaction was a pleasant golden yellow colour.

  1. Removed MeCN by rotary evaporation
  2. Dissolved in DCM (100 mL)
  3. Washed with water (2 x 125 mL)
  4. Washed with brine (100 mL)
  5. Dried over mag sulphate and rotovapped

Empty vial: 15.7933 Full vial: 17.3362 Mass: 1.5429 g, of which 1534 g is calculated to be mono or di bromo product. 99% conversion rate and 94% yield.

KlementineJBS commented 10 months ago

H NMR

KBS40-2 cr_1.zip KBS42-2 cr.pdf