Bromoform → 7-Bromobicyclo[4.2.0]octa-1,3,5-triene

온도

145 °C

In a 250 mL round bottomed flask equipped with a drying tube and a condenser, a solution of cycloheptatriene (30.7 g, 300 mmol), bromoform (25.3 g, 100 mmol), anhydrous K2CO3 (15.0 g, 109 mmol), and 18-crown-6 (0.75 g) was heated with stirring at 145° C. for 9-10 h. The solution was allowed to cool and diluted with an equal volume of acetone. Silica gel (15.0 g) was added to reaction mixture and the insoluble solid residue was separated via vacuum filtration and the filter cake washed with acetone until the washings were colorless. The filtrate was concentrated and distilled to remove residual cycloheptatriene. The viscous, brown residue was precipitated into hot petroleum ether. After filtration to remove the precipitate, the filtrate was concentrated and distilled in vacuo through a Vigreaux column to give slightly impure product. Pure 1-bromobenzocyclobutene was obtained as a light yellow liquid by redistillation yield (2.95 g, 5.94%). 1H NMR (300 MHz, CDCl3) δ 7.28 (m, 1H, ArH), 7.16 (d, 1H, J=7.0 Hz, ArH), 7.07 (d, 1H, J=6.4 Hz, ArH), 5.39 (m, 1H, CH), 3.85 (dd, 1H, J=4.4 Hz, J=14.7 Hz, CH2), 3.45 (d, 1H, J=14.7 Hz, CH2).

1. customIn a 250 mL round bottomed flask equipped with a drying tube and a condenser
2. temperatureto cool
3. additionSilica gel (15.0 g) was added to reaction mixture
4. customthe insoluble solid residue was separated via vacuum filtration
5. washthe filter cake washed with acetone until the washings
6. concentrationThe filtrate was concentrated
7. distillationdistilled
8. customto remove residual cycloheptatriene
9. customThe viscous, brown residue was precipitated into hot petroleum ether
10. filtrationAfter filtration
11. customto remove the precipitate
12. concentrationthe filtrate was concentrated
13. distillationdistilled in vacuo through a Vigreaux column
14. customto give slightly impure product

ORD 기록

ord-8ff38a025f3c48e3a0e22d3e6018f128

출처 데이터셋

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08492510B2