Acetic Acid → HCID 23150364, compound

HRID 550330Notes

Reaction equation

HRID 550330 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([Br:16])=[CH:10][CH:11]=3)[C:6](=[O:17])[C:5](=O)[C:4]=2[CH:3]=1.C[Mg]Cl.[C:22]([OH:25])(=O)[CH3:23]>C1COCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:13]2[C:12]3[C:7](=[CH:8][C:9]([Br:16])=[CH:10][CH:11]=3)[C:6]([OH:17])([CH3:5])[C:22]([OH:25])([CH3:23])[C:14]=2[CH:15]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2658432,7-dibromophenanthrene-9,10-dioneHCID 178418332HCID 178418332, compound

Product 1

HCID 23150364HCID 23150364, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

34.3 g (94 mmol) of 2,7-dibromophenanthrene-9,10-quinone were suspended in 600 ml of dry THF at −10° C. under argon, and 141 ml (282 mmol) of methylmagnesium chloride (2 molar solution in THF) were added dropwise at such a rate that the internal temperature did not exceed 0° C. The mixture was subsequently stirred overnight at room temperature. 50 ml of glacial acetic acid were added to the batch with ice cooling, and the mixture was diluted with ethyl acetate. After washing twice with saturated sodium chloride solution, the mixture was dried over sodium sulfate, and the solvents were removed, giving 43.4 g of the product, which was employed without further purification for the next step.

Workup

  1. customdid not exceed 0° C
  2. washAfter washing twice with saturated sodium chloride solution
  3. dry with materialthe mixture was dried over sodium sulfate
  4. customthe solvents were removed

Sources & evidence

ORD record
ord-c4a7e11ef2d44a2c8591bb5c18ab2929
Source dataset
uspto-grants-2011_05
Patent number
US07947382B2

Reaction notes

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