Реакция #1893136

Уравнение реакции

tert-butyl 2-(2,2-dimethylchroman-6-sulfonamido)acetate

BEMP

1-bromo-3-(bromomethyl)-5-fluorobenzene

→

powder

Выход 90.1%

tert-butyl 2-(N-(3-bromo-5-fluorobenzyl)-2,2-dimethylchroman-6-sulfonamido)acetate

Выход 90.1%

Растворители

MeCN

Условия реакции

Обработка

1. 1
   ФильтрацияThe reaction mixture was filtered
2. 2
   Промывкаrinsed alternatively by dichloromethane and methanol
3. 3
   КонцентрированиеThe filtrate was concentrated
4. 4
   Другоеto give a reddish orange residue, which
5. 5
   Другоеwas purified by silica chromatography

Методика

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)-5-fluorobenzene (501 mg, 1.871 mmol). The mixture was heated in a microwave synthesizer at 90° C. for 3 hours. The reaction mixture was filtered, rinsed alternatively by dichloromethane and methanol. The filtrate was concentrated to give a reddish orange residue, which was purified by silica chromatography to obtain a white powder (688 mg, 86% yield). 1H NMR (500 MHz, CDCl3) δ 7.56 (d, J=6.2 Hz, 2H), 7.18-7.12 (m, 2H), 6.95 (d, J=9.0 Hz, 1H), 6.87-6.80 (m, 1H), 4.46 (s, 2H), 3.82 (s, 2H), 2.80 (t, J=6.7 Hz, 2H), 1.83 (t, J=6.7 Hz, 2H), 1.36 (s, 9H), 1.35 (s, 6H). 19F NMR (471 MHz, CDCl3) δ LRMS [ESI, MH+] m/z calcd for C24H30BrFNO5S 542.10, found 542.1.

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