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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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2023_BG_3B_1 - Hydrolysis on 2-trifluoromethylaniline fragment #94

Closed KlementineJBS closed 11 months ago

KlementineJBS commented 1 year ago

Reaction scheme

2023_BG_3B

Outcome

527 mg (2.40 mmol, 94%)

KlementineJBS commented 1 year ago
  1. Dissolved SM (827.6 mg, 2.55 mmol) in NaOH (2.5 M, 4 mL)
  2. Heated to 80 C at 3.30 pm

TLC indicated completion at 4.10 pm.

Unlike when this reaction was performed on other substrates, no precipitate had formed.

  1. Extracted with ethyl acetate (3 x 20 mL)
  2. Washed with brine and dried over mag sulphate
  3. Rotovapped down
KlementineJBS commented 1 year ago

LRMS

Peak at 219.02 [M-H]-.

2023_BG_3B_1.pdf 2023_BG_3B_1.d.zip

KlementineJBS commented 1 year ago

vial: 16.0330 Full vial: 16.5600 Mass: 527 mg (2.40 mmol, 94%)

KlementineJBS commented 1 year ago

H NMR

1H NMR (300 MHz, DMSO) δ 9.23 (s, 1H) 7.68 (q, 1H), 7.55 (d, 1H), 7.46 (t, 1H).

Why are amine peaks not present?

2023_BG_3B_1_1.zip 2023_BG_3B_1.pdf

KlementineJBS commented 12 months ago

NMR

1H NMR (500 MHz, DMSO-d6) δ 9.25 (s, 1H), 7.72 (dd, J = 8.0, 1.5 Hz, 1H), 7.68 (td, J = 7.7, 1.5 Hz, 1H), 7.57 (d, J = 8.0 Hz, 1H), 7.50 – 7.45 (m, 1H).

13C NMR (126 MHz, DMSO) δ 183.57, 137.41, 133.16, 132.36, 127.47, 127.28, 126.49 (q), 125.91 (q), 125.11, 122.93, 120.76.

19F NMR (471 MHz, DMSO) δ -59.56.

230709_3B_1.zip 230709_3B_2.zip 230709_3B_3.zip 2023_BG_3B 500 MHz.pdf