Benzofuran, 5-bromo- → 5-Isobutylbenzofuran

온도

100 °C

5-bromobenzofuran (500 mg, 2.56 mmol) was dissolved in THF solution of isobutylzinc(II)bromide (0.5M, 15 mL, 7.40 mmol) in a microwave reaction tube. Pd(PtBu3)2 (65 mg, 0.128 mmol, 0.05 eqv.) was added to this solution. The mixture was purged with N2 gas for 3-5 min and heated at 100° C. for 30 min under microwave irradiation. Upon completion of the reaction, the reaction mixture was diluted with ethyl acetate, washed with 1N HCl aqueous solution, brine, filtered through Celite. The filtrate was dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography (ISCO system, 5% EtOAc in hexanes) to give 0.331 g desired product (74% yield): 1H NMR (400 MHz, CDCl3) δ 7.59 (s, 1H), 7.35 (d, 1H), 7.07 (d, 1H), 6.70(s, 1H), 2.59 (d, 2H), 1.9 (m, 1H), 0.9 (d, 6H).

1. customThe mixture was purged with N2 gas for 3-5 min
2. customUpon completion of the reaction
3. washwashed with 1N HCl aqueous solution, brine
4. filtrationfiltered through Celite
5. dry with materialThe filtrate was dried over Na2SO4
6. concentrationconcentrated
7. customThe residue was purified by silica gel column chromatography (ISCO system, 5% EtOAc in hexanes)

ORD 기록

ord-014d8931a676473cbb01f4a78700f58e

출처 데이터셋

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07855193B2