Tetrahydrofuran → 2-Bromo-9,9-dimethoxyethylfluorene

To a solution of 2-bromofluorene (2.45 g, 10 mmol) in tetrahydrofuran (dry, 75 ml) was added potassium t-butoxide (3.36 g, 30 mmol), giving a deep orange solution. The mixture was stirred at ambient temperature for 10 min and added 2-methoxyethyl mesylate in tetrahydrofuran dropwise. Exothermic reaction was observed. Stirring was continued at ambient temperature for overnight to give an orange solution. At the end of the reaction, it was diluted with water (150 ml). The products extracted with ethylacetate (30 ml) and washed with water. Organic layer was dried over magnesium sulfate and concentrated in vacuuo to afford the crude product. It was purified by preparative thin layer chromatography (silica gel, Rf=0.3 using hexane-EtOAc/3:2 as eluent) to give 2-bromo-9,9-dimethoxyethylfluorene (3.3 g).

1. customgiving a deep orange solution
2. customExothermic reaction
3. stirringStirring
4. waitwas continued at ambient temperature for overnight
5. customto give an orange solution
6. customAt the end of the reaction, it
7. extractionThe products extracted with ethylacetate (30 ml)
8. washwashed with water
9. dry with materialOrganic layer was dried over magnesium sulfate
10. concentrationconcentrated in vacuuo
11. customto afford the crude product
12. customIt was purified by preparative thin layer chromatography (silica gel, Rf=0.3 using hexane-EtOAc/3:2 as eluent)

ORDレコード

ord-67040ca6b49542a6ac6a7c0f8ef870c1

出典データセット

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07132572B2