2-Bromophenol → Anthracene

温度

-30 °C

A solution of 9-bromoanthracene (0.67 g, 2.6 mmol, 1.2 eq) in dry Et2O (13 mL) under N2 was cooled to −30° C. and nBuli (1.6 M in hexane, 1.6 mL, 2.6 mmol, 1.2 eq) was added dropwise. The solution was stirred for 20 min. at −30° C. followed by dropwise addition of ZnCl2 (0.50 M in THF, 5.2 mL, 2.6 mmol, 1.2 eq). The reaction was stirred and warmed to RT over 30 min. The volatiles were removed under N2 purge and the residue was redissolved in 3:1 THF/NMP (11 mL). The MOM-protected bromophenol (2.2 mmol, 1.0 eq) and Pd(PtBu3)2 (22 mg, 44 μmol, 4 mol %) were added and the reaction was heated to 100° C. for 2 h. The reaction was cooled to RT and the THF was removed. The residue was diluted with CH2Cl2, washed with 1 M HCl, and dried over Na2SO4. The crude material was purified by flash chromatography.

1. stirringThe reaction was stirred
2. temperaturewarmed to RT over 30 min
3. customThe volatiles were removed under N2
4. custompurge
5. dissolutionthe residue was redissolved in 3:1 THF/NMP (11 mL)
6. temperaturethe reaction was heated to 100° C. for 2 h
7. temperatureThe reaction was cooled to RT
8. customthe THF was removed
9. additionThe residue was diluted with CH2Cl2
10. washwashed with 1 M HCl
11. dry with materialdried over Na2SO4
12. customThe crude material was purified by flash chromatography

ORDレコード

ord-2b9cd45206bd483889c44f0a2aa70c02

出典データセット

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07091292B2