Table 4. Synthesis of Polydeuterated IAA and IBA in an Economical Way^a.

entry	substrate	solvent	time (h)	D content (%)b	yield (%)c
1	2	70% CD3OD/D2O	5	97	99
2d	2	CH(OCH3)3/D2Oe	5	97	95
3d	3	CH(OCH3)3/D2Oe	14	97	94

^aReactions were performed in 20 wt % D₂SO₄ in CD₃OD/D₂O (7/3, 0.2 M). After the reaction was completed, the mixture was poured into an aqueous LiOH solution to hydrolyze.

^bIndicated as the average D content at C2 and C4–C7, which were calculated based on the ¹H NMR spectra of the isolated product.

^cIsolated yield.

^dReactions were performed on a 1 gram scale of the substrate.

^eIn situ preparation of 20 wt % D₂SO₄ in CD₃OD/D₂O (7/3).