2023_BG_2B_3 - Hydrolysis on 3-fluoroaniline fragment

[KlementineJBS]

Reaction scheme

Outcome

4.8941 g (28.8 mmol, 63%)

[KlementineJBS]

1. Dissolved SM (2023_BG_2A, 12.44 g, 45.4 mmol) in NaOH (2.5 M, 100 mL)
2. Heated to 80 C with stirring and left from 11.25 am. Added a little extra water to wash down material from sides of RBF
3. Mixture was initially a bright yellow colour but went paler after ~40 minutes of stirring.

TLC indicated completion.

20% ethyl acetate in hexane

Work up as usual - see step 2.

[KlementineJBS]

LRMS

Peaks at 169. 04 [M-H]- and 204.99 [M+Cl]- confirm product is present. Still unsure what peak at 135 represents.

2023_BG_2B_3.d.zip 2023_BG_2B_3.pdf

[KlementineJBS]

Vial 1 empty: 15.2846 Vial 1 full: 19.5344 Mass: 4.2498 g

Vial 2 empty: 15.534 Vial 2 full: 16.1797 Mass: 0.6443 g

Total mass: 4.8941 g (28.8 mmol, 63%)

Consider extracting aqueous filtrate?

[KlementineJBS]

H NMR

Performed an extraction on the aqueous filtrate using ethyl acetate. Got a thick yellow oil - NMR indicated that this oil contained a small amount of product but was largely ethyl acetate. Upon sitting over the weekend, a large chunk of white solid precipitated out - this is presumed to be sodium carbonate and/or NaCl used in the workup process.

H NMR of extract 2023_BG_2B_3_1.zip 2023_BG_2B_3.pdf