Sodium hydride → HCID 57348179, compound

HRID 486233Notes

Reaction equation

HRID 486233 reaction equation
[C:1](Cl)(=[O:11])[CH2:2][CH:3]([CH2:7][C:8](Cl)=[O:9])[C:4](Cl)=[O:5].[Br:13][C:14]1[CH:26]=[C:25]([Br:27])[CH:24]=[C:16]([C:17]([O:19]C(C)(C)C)=O)[C:15]=1[OH:28].[H-].[Na+]>O1CCCC1.FC(F)(F)C(O)=O>[Br:13][C:14]1[CH:26]=[C:25]([Br:27])[CH:24]=[C:16]([CH2:17][O:19][C:1](=[O:11])[CH2:2][CH:3]([CH2:7][C:8]([O:19][CH2:17][C:16]2[C:15](=[C:14]([Br:13])[CH:26]=[C:25]([Br:27])[CH:24]=2)[OH:28])=[O:9])[C:4]([O:19][CH2:17][C:16]2[C:15](=[C:14]([Br:13])[CH:26]=[C:25]([Br:27])[CH:24]=2)[OH:28])=[O:5])[C:15]=1[OH:28]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 13806986HCID 13806986, compoundHCID 15931183tert-Butyl 3,5-dibromo-2-hydroxybenzoate

Product 1

HCID 57348179HCID 57348179, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  1. customthe solvent was then removed under reduced pressure
  2. dissolutionThe residue was dissolved in diethyl ether
  3. extractionextracted several times with water
  4. dry with materialThe extract was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customRecrystallization from ethanol
  8. customgave a pure product
  9. customto stand at room temperature
  10. waitAfter 30 minutes
  11. customthe solvent was removed under reduced pressure
  12. customthe precipitate recrystallized from trifluoroacetic acid

Sources & evidence

ORD record
ord-90c75096f1ef436ca676d73e76642148
Source dataset
uspto-grants-1994_03
Patent number
US05290919

Reaction notes

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