반응 #435410

반응 방정식

9-bromo—N-(2,6-diisopropylphenyl)perylene-3,4-dicarboximide

6-acetoxy-1-hexyne

hydrochloric acid

→

N-(2,6-diisopropylphenyl)-9-(6-acetoxy-1-hexynyl)perylene-3,4-dicarboximide

수율 90.0%

용매

—

mixture

tetrahydrofuran

piperidine

반응 조건

후처리

1. 1
   온도After cooling to room temperature
2. 2
   workup.ADDITIONthe reaction mixture was added to three times
3. 3
   기타the organic phase was separated off
4. 4
   추출the aqueous phase was extracted with 3 times 200 ml of methylene chloride
5. 5
   건조the combined organic extracts were dried over magnesium sulfate
6. 6
   기타the solvent was removed under reduced pressure

실험 절차

2.0 g (3.56 mmol) of 9-bromo—N-(2,6-diisopropylphenyl)perylene-3,4-dicarboximide (prepared in analogy to Example 6a of WO 96/22 332 using N-(2,6-diisopropylphenyl)perylene-3,4-dicarboximide from Example 28 of WO 97/22 607 as starting material) was dissolved in 500 ml of a mixture of one part by volume of absolute tetrahydrofuran (THF) and one part by volume of dry piperidine under inert gas, admixed in succession with 4 mol % of Pd(PPh3)4 (164 mg, 0.14 mmol), 5 mol % of CuI (32 mg, 0.18 mmol) and 1.14 g (7.12 mmol) of 6-acetoxy-1-hexyne; this mixture was slowly heated to 70° C. and held at this temperature for 1 h. After cooling to room temperature, the reaction mixture was added to three times the volume of a mixture of ice and concentrated hydrochloric acid in a volume ratio of 3:1, the organic phase was separated off, the aqueous phase was extracted with 3 times 200 ml of methylene chloride, the combined organic extracts were dried over magnesium sulfate and the solvent was removed under reduced pressure. Chromatography on silica gel using methylene chloride as eluent gave 1.98 g (90%) of N-(2,6-diisopropylphenyl)-9-(6-acetoxy-1-hexynyl)perylene-3,4-dicarboximide as a red powder having a melting point >300° C.

출처