Synthesis
The general procedure for the synthesis of tert-butyl iodoacetate from tert-butyl bromoacetate was as follows: tert-butyl bromoacetate (6) (1.00 g, 5.13 mmol, 1.0 eq.) was slowly added dropwise to a pre-prepared solution of sodium iodide (1.15 g, 7.69 mmol, 1.5 eq.) in anhydrous acetone (30 mL). The reaction mixture was stirred continuously at room temperature for 150 min and the progress of the reaction was monitored by thin layer chromatography (TLC) [unfolding agent: petroleum ether/ethyl acetate = 2:1; Rf value of tert-butyl iodoacetate = 0.73] to confirm the complete conversion of the reaction. Subsequently, the reaction solution was filtered to remove insoluble impurities and the filtrate was concentrated by rotary evaporator. To the concentrated residue, pentane (15 mL) was added for washing and the filtrate was filtered again to remove the precipitate. Finally, the filtrate was concentrated under vacuum to afford the target product tert-butyl iodoacetate (1.01 g, 81% yield) as a light yellow oil.
References
[1] Patent: US5618808, 1997, A
[2] Angewandte Chemie - International Edition, 2010, vol. 49, # 15, p. 2738 - 2742
[3] Journal of Organic Chemistry, 2006, vol. 71, # 19, p. 7307 - 7314
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 1997, vol. 39, # 6, p. 509 - 524
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7735 - 7738
