Toluene → HCID 59279019, compound

HRID 221943Notes

Reaction equation

HRID 221943 reaction equation
C([O:4][C:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17](OC(C)C)=[O:18])=[CH:9][C:8]=1[Br:23])=O)(C)C.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[Cl-].[NH4+]>ClCCl>[Br:23][C:8]1[CH:9]=[C:10]([CH2:17][OH:18])[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]=1[CH2:5][OH:4]

Participants

6

Reactant 4

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 59488757HCID 59488757, compound

Product 1

HCID 59279019HCID 59279019, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen stream, to a solution of 2-bromo-naphthalene-1,4-dicarboxylic acid diisopropyl ester (191.5 mg, 0.505 mmol) in dichloromethane (1.9 mL) was added a solution of diisobutylaluminum hydride in toluene (1.04 M, 4.9 mL, 5.096 mmol) at −78° C. The temperature of the resultant mixture was raised over 2 hours to 0° C., and then to the solution was added saturated aqueous ammonium chloride to stop the reaction. The resultant mixture was twice extracted with ethyl acetate. After drying the organic layer over anhydrous magnesium sulfate, solvent was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:1)), to thereby obtain the titled compound (124 mg, 87%).

Workup

  1. customthe reaction
  2. extractionThe resultant mixture was twice extracted with ethyl acetate
  3. dry with materialAfter drying the organic layer over anhydrous magnesium sulfate, solvent
  4. customwas removed by distillation under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:1))

Sources & evidence

ORD record
ord-230947c018eb46a5b4137a2cae6359ab
Source dataset
uspto-grants-2012_06
Patent number
US08207134B2

Reaction notes

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