. 2020 May 8;22(11):4123–4128. doi: 10.1021/acs.orglett.0c01200

Table 1. Regioselective Synthesis of 2a^a.

entry	Cl source	solvent	yield (%)	2a:2a′:2a″
1	SOCl₂	THF	78	82:12:6
2	SOCl₂	Et₂O	83	76:16:8
3	SOCl₂	CH₂Cl₂	83	88:12:–
4	SOCl₂^b	CH₂Cl₂	47	80:14:6
5	PCl₃	CH₂Cl₂	80	96:4:–
6	PCl₅	CH₂Cl₂	50	98:2:–
7	POCl₃	CH₂Cl₂	52	12:–:–^c
8	NCS/PPh₃^d	CH₂Cl₂	40	94:6:–
9	NCS/PPh₃^d	THF	67	>99:–:–

Unless otherwise noted, 1a (0.1 mmol, 0.1 M) and the chlorinating agent (0.1 mmol) at 0 °C overnight.

With 0.1 mmol of pyridine.

An unknown product was formed.

NCS (0.15 mmol) and PPh₃ (0.15 mmol).

Table 1. Regioselective Synthesis of 2aa.