Reaktion #573415

Reaktionsgleichung

NaH

Tricarballylic trichloride

tert-butyl 3,5-dibromosalicylate

→

Tris(3,5-dibromosalicyl)-tricarballvlate

Lösungsmittel

trifluoroacetic acid

THF

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solvent was then removed under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in diethyl ether
3. 3
   Extraktionextracted several times with water
4. 4
   TrocknenThe extract was dried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeRecrystallization from ethanol
8. 8
   Sonstigegave a pure product
9. 9
   Sonstigeto stand at room temperature
10. 10
    workup.WAITAfter 30 minutes
11. 11
    Sonstigethe solvent was removed under reduced pressure
12. 12
    Sonstigethe precipitate recrystallized from trifluoroacetic acid

Vorschrift

Tricarballylic trichloride (0.01 mol) (see Emery, Ber., 22:2921 (1989)) in dry tetrahydrofuran (THF) (10 ml) was added dropwise to three equivalents of tert-butyl 3,5-dibromosalicylate (see Delaney et al, Arch. Biochem. Biophys., 28:627 (1984)) previously been treated with a stoichiometric amount of NaH in THF. The mixture was stirred for 5 hours at room temperature, and the solvent was then removed under reduced pressure. The residue was dissolved in diethyl ether and extracted several times with water. The extract was dried over MgSO4, filtered and concentrated. Recrystallization from ethanol gave a pure product; m.p. 100-102° C. The resulting product (2 mmol) was dissolved in anhydrous trifluoroacetic acid (10 ml) and allowed to stand at room temperature. After 30 minutes, the solvent was removed under reduced pressure and the precipitate recrystallized from trifluoroacetic acid; m.p. 186° C. (see Razynska et al, supra).

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