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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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KBS39-1 - NBS reaction on KBS37 #119

Closed KlementineJBS closed 9 months ago

KlementineJBS commented 11 months ago

Link to HIRAC and master page.

HIRAC NBS reaction Breaking Good.docx

Reaction scheme

KBS39 - NBS reaction on KBS37

Outcome

41.4 mg, 32%

KlementineJBS commented 11 months ago
  1. Dissolved KBS37 (#118 , 79.6 mg, 0.465 mmol), tosic acid (141.3 mg, 0.743 mmol, 1.6 equiv.) and NBS (101.5 mg, 0.570 mmol, 1.2 equiv.) in MeCN (25 mL)
  2. Stirred at 82 C from 3.30 pm
KlementineJBS commented 11 months ago

TLC on Wednesday indicated reaction was occuring. Uncertain which spot is what.

Turned off on Wednesday 26th ~6pm.

  1. Removed MeCN via rotary evaporation
  2. Dissolved in DCM (12 mL)
  3. Washed with water (2 x 10 mL) and brine (10 mL)
  4. Dried over mag sulphate and rotovapped down

Vial: 15.8062 Full vial: 15.8905 Mass: 84.3 mg

Moles of product calculated as 0.148 mmol, 32%.

KlementineJBS commented 11 months ago

H NMR

Indicates approximately 50% conversion to mono-bromo product. (Peak at 2.91 represents methyl in SM, peak at 5.07 indicates methylene in product.)

KBS39-1 crude.pdf KBS39-1 cr_1.zip Bromination percentage calculations.xlsx