Tetrahydrofuran → HCID 20403100, compound

HRID 2164718Notes

Reaction equation

HRID 2164718 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].Br[C:6]1[C:7](=[O:18])[C:8]2[C:13]([C:14](=[O:17])[C:15]=1[Br:16])=[CH:12][CH:11]=[CH:10][CH:9]=2.[NH4+].[Cl-].[CH2:21]1[CH2:25]O[CH2:23][CH2:22]1>[Cl-].[Cl-].[Zn+2]>[CH2:23]([C:6]1[C:7](=[O:18])[C:8]2[C:13]([C:14](=[O:17])[C:15]=1[Br:16])=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:22][CH2:21][CH2:25][CH2:8][CH2:7][CH2:6][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 832592,3-Dibromo-1,4-naphthoquinoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20403100HCID 20403100, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

To 0.155 g (1.16 mmoles) of AlCl3 in 20 mL of THF was added 5.0 g (3.48 mmoles) of dodecyl MgBr (0.697 mmole/g). This mixture was added to 1.00 g (3.17 mmoles) of 2,3-dibromo-1,4-naphthoquinone in 50 mL of THF. A brown solution was obtained. Then, 0.40 g (2.94 mmoles) of ZnCl2 was added and the mixture was stirred overnight. The mixture was poured into 100 mL of NH4Cl solution, extracted with 3×50 mL of ether, dried over MgSO4, filtered, and solvent was removed. The residue was flash-chromatographed (on silica, toluene eluant). Thus, 0.390 g (0.76 mmole, 24%) of 2-n-dodecyl-3-bromo-1,4-naphthoquinone was obtained. mp 98° to 100° C. 1H NMR (δ, CDCl3): 8.11 (m,2H), 7.70 (m,2H), 2.90 (m,2H), 1.33 (br. s,20H), 0.90 (m,3H). IR (cm-1, CHCl3): 1678s, 1599m, 1579w, 1280s.

Workup

  1. customA brown solution was obtained
  2. extractionextracted with 3×50 mL of ether
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customsolvent was removed
  6. customThe residue was flash-chromatographed (on silica, toluene eluant)

Sources & evidence

ORD record
ord-a5496e3940b34427b9c8eacdd9fdd4a5
Source dataset
uspto-grants-1985_03
Patent number
US04507241

Reaction notes

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