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. Author manuscript; available in PMC: 2020 Apr 29.
Published in final edited form as: European J Org Chem. 2019 Aug 24;2019(39):6597–6605. doi: 10.1002/ejoc.201901033

Table 3.

Halogen exchange on α-fluoroglycine esters 4a.

graphic file with name nihms-1056468-t0011.jpg
Entry[a] Conditions Time Temp % Conv.[b] % Yield[b,c]
1 TMSCl (66 mol%) 2 h 0 °C 72 45
2 TMSCl (100 mol%) 2 h 0 °C 82 82
3 TMSCl (130 mol%) 30 mins −78 °C 23 20
4 TMSCl (130 mol%) TA (10 mol%) 30 mins − 78 °C 60 60
5 TMSCl (130 mol%) TA (10 mol%) 1 h − 78 °C 100 96[c]
[a]

Reactions run on a 0.25 mmol scale.

[b]

Conversions and Yields determined by 1H NMR on crude reaction mixtures using mesitylene as internal standard.

[c]

Isolated yield.