An oven-dried (110 °C), three-necked, 1-L round-bottomed flask is equipped with a 1.25-inch egg-shaped magnetic stirring bar and three rubber septa, 
one containing a temperature probe and another a nitrogen inlet. 
Solid (diacetoxyiodo)benzene ("DIB," 23.9 g, 74.2 mmol, 1.35 equiv) (Note 1) is added under purging N2 followed by CH3CN (480 mL). 
The flask is <purged> for <5 min> and the contents are maintained under <inert atmosphere> during all subsequent operations. 
The stirrer is set to <560 rpm> and neat trifluoroacetic acid (TFA, 6.4 mL, 83.6 mmol, 1.5 equiv) is carefully added via <syringe> over <3 min> at <room temperature>, w
hereupon the mixture becomes <homogeneous>.
A solution of methyl 4-hydroxyphenylacetate (1) (9.1 g, 54.8 mmol, 1.0 equiv) in CH3CN (20 mL), 
prepared in a flame-dried 50-mL round-bottomed <flask>, is added to the DIB solution over <3 h> via <syringe pump>. 
During the addition, the tip of the needle is <immersed> into the solution to a depth of <0.5 inch> and the progress of the reaction is followed by TLC. 
At the end of the addition, the solution turns <light brown>. 
The mixture is <transferred> to a one-necked 1-L round-bottomed <flask> and 
concentrated under <reduced pressure> (mechanical pump vacuum, 175 mmHg) at 32 °C (rotary evaporator bath temperature). 
Toluene (10 mL) is then added and the resulting suspension is <concentrated> under <reduced pressure> to azeotropically remove residual TFA. 
Addition of toluene and evaporation are repeated <twice> again to ensure <removal> of essentially all of the <TFA>.


