Sodium hydride → HCID 9853605, compound

Participants

Reaction Steps

A mixture of diethyl 2,5-dihydroxyterephthalate (127 mg, 0.5 mmol) and sodium hydride (60%, 20 mg) in tetrahydrofuran (1.5 mL) was stirred at room temperature for 30 minutes followed by the addition of 1-chloro-2-nitro-4-trifluoromethanesulfonyl-benzene (75 mg, 0.26 mmol). After 45 mintues, more 1-chloro-2-nitro-4-trifluoromethanesulfonyl-benzene (63 mg, 0.22 mmol) was added. Tetrahydrofuran (1 mL) was added after each addition of 1-chloro-2-nitro-4-trifluoromethanesulfonyl-benzene. After 18 hours at room temperature, more 1-chloro-2-nitro-4-trifluoromethanesulfonyl-benzene (75 mg) was added and the temperature was increased to 60° C. for 2 hours. The reaction was diluted with chloroform/isopropanol, washed with brine and purified on silica gel to give the title compound. 1H NMR (360 MHz, DMSO-d6) δ 8.82 (d, J=2.2 Hz, 2H), 8.27 (dd, 2H), 8.18 (s, 2H), 7.48 (d, J=9 Hz, 2H), 4.15 (q, J=6.8 Hz, 4H), 0.98 (t, J=6.8 Hz, 6H).

Provenance & Evidence