Butyl ether → HCID 87234478, Verbindung

Temperatur

-78 °C

Di-acylation (Step A) A suspension of (2,3,5,6-tetrabromothieno[3,2,b]thiophene (20 mmol) in anhydrous THF (200 mL) is cooled to −78° C. Phenyl lithium solution in n-butyl ether (41 mmol) is added dropwise and the reaction mixture is stirred at −78° C. for 4 h. Docosanoyl chloride (41 mmol) is added to the reaction mixture via syringe while maintaining the temperature of the mixture as close to −78° C. The reaction is allowed to warm to RT over about three hours and then stirred overnight at RT. The reaction mixture is then quenched by the addition of crushed ice (200 g). The reaction mixture is stirred while the ice is allowed to melt. Most (>90%) of the THF is then removed under reduced pressure and the solid is filtered from the residual solution. The solid is suspended in water (100 mL) and stirred for 1 hr then filtered. The solid is re-suspended in methanol (100 mL), stirred for 1 hr then filtered to give the product 1-{3,6-dibromo-5-docosanoylthieno[3,2-b]thiophen-2-yl}docosan-1-one. 1H NMR (CD2Cl2) δ 0.95-1.15 (6H, m), 1.30-1.82 (76H, m) and 3.17-3.32 (4H, m).

1. temperaturewhile maintaining the temperature of the mixture
2. customas close to −78° C
3. temperatureto warm to RT over about three hours
4. stirringstirred overnight at RT
5. customThe reaction mixture is then quenched by the addition of crushed ice (200 g)
6. stirringThe reaction mixture is stirred while the ice
7. customMost (>90%) of the THF is then removed under reduced pressure
8. filtrationthe solid is filtered from the residual solution
9. stirringstirred for 1 hr
10. filtrationthen filtered
11. stirringstirred for 1 hr
12. filtrationthen filtered

ORD-Eintrag

ord-9cf8397637c242c1b3d932f72b0d1a57

Quelldatensatz

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08217183B2