3-Bromobenzyl bromide → tert-butyl 2-(N-(3-bromobenzyl)-2,2-dimethylchroman-6-sulfonamido)acetate

関与物質

反応条件

反応手順

To the solution of tert-butyl 2-(2,2-dimethylchroman-6-sulfonamido)acetate (500 mg, 1.407 mmol) in MeCN (15 mL) was added resin-supported BEMP (786 mg, 1.547 mmol) and 1-bromo-3-(bromomethyl)benzene (598 mg, 2.391 mmol). The mixture was heated in a microwave synthesizer at 90° C. for 3 hours. The reaction mixture was filtered, rinsed alternatively with dichloromethane and methanol. The filtrate was concentrated to give a reddish orange residue, which was purified by silica chromatography to obtain a white powder (620 mg, 84% yield). 1H NMR (500 MHz, CDCl3) δ 7.60-7.54 (m, 2H), 7.40 (d, J=7.4 Hz, 1H), 7.35 (s, 1H), 7.19 (dt, J=15.1, 7.6 Hz, 2H), 6.88-6.81 (m, 1H), 4.47 (s, 2H), 3.80 (s, 2H), 2.80 (t, J=6.7 Hz, 2H), 1.83 (t, J=6.7 Hz, 2H), 1.35 (s, 6H), 1.35 (s, 9H). LRMS [ESI, MH+] m/z calcd for C24H31BrNO5S 524.11, found 524.1.

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