Water → HCID 21874553, compound

HRID 733006Notes

Reaction equation

HRID 733006 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][Br:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:12]([Mg]Cl)([CH3:14])[CH3:13].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.O>C1COCC1>[CH:12]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])[CH2:8][Br:9])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 660114-Nitrobenzyl bromideHCID 178418918HCID 178418918, compound

Product 1

HCID 21874553HCID 21874553, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-nitrobenzyl bromide (432 mg, 2 mmol) in THF (5 mL) at −70° C., was treated dropwise with isopropylmagnesium chloride (1 mL, 2-M in Et2O, 2 mmol), stirred for 1 h, treated with DDQ (499 mg, 2.2 mmol) and stirred at room temperature for 16 h. The reaction mixture was poured into water (10 mL), extracted with EtOAc (2×10 mL), dried (MgSO4), concentrated in vacuo and filtered. The resulting solid was purified by chromatography [SiO2; EtOAc:Heptane (1:4)] to give the title compound (183 mg, 35%) as a pale yellow solid which was used in the next reaction without further purification.

Workup

  1. stirringstirred at room temperature for 16 h
  2. extractionextracted with EtOAc (2×10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. filtrationfiltered
  6. customThe resulting solid was purified by chromatography [SiO2; EtOAc:Heptane (1:4)]

Sources & evidence

ORD record
ord-96bebde1f0d94476a42f3ba944d22dc0
Source dataset
uspto-grants-2009_09
Patent number
US07589097B2

Reaction notes

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