The solvolysis rate constants of 2,2,2-trichloroethyl chloroformate ($Cl_3CCH_2OCOCl$, $mathbf{3}$) in 30 different solvents are well correlated with the extended Grunwald-Winstein equation, using the $N_T$ solvent nucleophilicity scale and the $Y_{Cl}$ solvent ionizing scale, with sensitivity values of $1.28{pm}0.06$ and $0.46{pm}0.03$ for $l$ and $m$, respectively. The activation enthalpies (${Delta}H^{ eq}$) are 10.1 to 12.8 $kcal{cdot}mol^{-1}$ and the activation entropies (${Delta}S^{ eq}$) are -27.8 to -36.8 $cal{cdot}mol^{-1}{cdot}K^{-1}$, which is consistent with the proposed bimolecular reaction mechanism. The kinetic solvent isotope effect ($k_{MeOH}/k_{MeOD}$) of 2.39 is also in accord with $S_N2$ mechanism probably assisted by general-base catalysis.