1,2-Dichlorobenzene → HCID 25154393, compound

Participants

Reaction Steps

To a solution of 29 (60 mg, 0.77 mmol) in a mixture of MeOH (2.4 mL) and THF (0.8 mL) were added Pd(OH)2/C (25 mg) and 1,2-dichlorobenzene (60 μL). A balloon of hydrogen gas was attached for 0.5 hours with vigorous stirring. LC/MS indicated that de-protection was complete. The reaction mixture was filtered through Celite, concentrated to a residue, and purified by preparatory TLC (5% MeOH in DCM) to give 30 (23 mg, 71.2%). 1H NMR (300 MHz, CD3OD) δ 7.18 (s, 1H), 7.07 (s, 4H), 6.82 (s, 1H), 4.68 (d, J=10.2 Hz, 1H), 4.59 (d, J=9.9 Hz, 1H), 3.99 (m, 2H), 3.59-3.80 (m, 3H), 3.28-3.37 (m, 3H), 2.58 (q, J=7.5 Hz, 2H), 1.19 (t, J=7.5 Hz, 3H).

Provenance & Evidence