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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → t-Butyl 3-acetoxy-5-methyl-4-nitrophenylacetate

HRID 1357868
Notes
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Reaction equation

HRID 1357868 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])(=[O:3])[CH3:2].[CH3:22][Mg]Cl.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCCC1.C(OCC)C>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:8]=[C:9]([CH3:22])[C:10]=1[N+:11]([O-:13])=[O:12])(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 18188103t-Butyl 3-acetoxy-4-nitrophenylacetateHCID 178418332HCID 178418332, compound2×

Product 1

HCID 18188096t-Butyl 3-acetoxy-5-methyl-4-nitrophenylacetate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×
HCID 8028
Tetrahydrofuran
Solvent

Procedure

A stirred solution of t-butyl 3-acetoxy-4-nitrophenylacetate (8.0 g, Reference Example 18) in tetrahydrofuran (350 mL) at −15° C. under argon was treated dropwise with methyl magnesium chloride solution in diethyl ether (7 mL, 3M) and after 2 hours a further aliquot of methyl magnesium chloride solution in diethyl ether (7 mL, 3M). After stirring for a further 1 hour the reaction mixture was treated with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (10.4 g), then stirred at room temperature overnight, then partially evaporated and then treated with dichloromethane. The mixture was washed with water, then dried and then evaporated. The residue was subjected to flash chromatography on silica eluting with dichloromethane to give the title compound (1.66 g) as a yellow oil.

Workup

  1. stirringstirred at room temperature overnight
  2. custompartially evaporated
  3. additiontreated with dichloromethane
  4. washThe mixture was washed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-c71e9d00b83b43c1afcf78da9f6e3af0
Source dataset
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06593354B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes