Reaktion #42160

Reaktionsgleichung

dicyclohexylamine

1-bromo-4-fluorobenzene

2-methyl-3-butyne-2-ol

sodium chloride

→

(4-fluorophenyl)-2-methyl-3-butyne-2-ol

Ausbeute 97.0%

Lösungsmittel

toluene

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 50-ml four-necked flask was equipped with a stirrer
2. 2
   workup.ADDITIONadded into the flask
3. 3
   SonstigeThe flask was purged with argon
4. 4
   workup.STIRRINGby stirring at 30° C. for 30 minutes
5. 5
   workup.STIRRINGby stirring at 30° C. for 17 hours
6. 6
   workup.ADDITIONwere added
7. 7
   Sonstigefollowed by separation
8. 8
   SonstigeThe organic phase was purified by column chromatography

Vorschrift

A 50-ml four-necked flask was equipped with a stirrer, a thermometer and a reflux condenser. 0.034 g (0.15 mmol) of palladium (II) acetate, 1.088 g (6 mmol) of dicyclohexylamine and 5 ml of tetrahydrofuran were weighed in the flask, followed by stirring. Further, 0.157 g (0.3 mmol) of tri-tert-butylphosphonium tetraphenylborate obtained in Example A-1 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 30° C. for 30 minutes. 0.875 g (5 mmol) of 1-bromo-4-fluorobenzene and 0.505 g (6 mmol) of 2-methyl-3-butyne-2-ol were added, followed by stirring at 30° C. for 17 hours. After the completion of the reaction, 10 ml of tetrahydrofuran, 5 ml of toluene and 15 ml of saturated sodium chloride solution were added, followed by separation. The organic phase was purified by column chromatography to afford 0.864 g of (4-fluorophenyl)-2-methyl-3-butyne-2-ol (yield: 97 mol % based on 1-bromo-4-fluorobenzene). The identification of the product was made by 1H-NMR and 13C-NMR.

Quelle