تفاعل #435410

معادلة التفاعل

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

المردود 90.0%

المذيبات

—

mixture

tetrahydrofuran

piperidine

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر