2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-Methyl-2-nitrodibenzothiophene

HRID 1064025Notes

Reaction equation

HRID 1064025 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]2[S:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=1)([O-:3])=[O:2].[CH3:17][Mg]Cl.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1COCC1.O>[CH3:17][C:5]1[C:6]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[S:8][C:7]=2[CH:15]=[CH:16][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 95072Dibenzothiophene, 2-nitro-HCID 178418332HCID 178418332, compound

Product 1

HCID 222777981-Methyl-2-nitrodibenzothiophene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 2-nitrodibenzothiophene (2.20 g, 9.61 mmol) in dry THF (100 ml) at −15° C. was slowly added methyl magnesium chloride (3 M solution in THF; 9.6 ml, 29 mmol). After stirring at this temperature for 5.5 h, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (6.98 g, 30.75 mmol) was added portion wise, keeping the temperature below −10° C. The mixture was allowed to warm to room temperature and stirred for 16 h. The reaction mixture was diluted with water and extracted into DCM. The organic layers were further washed with water, dried and purified by chromatography (eluent—50% DCM /isohexane) to give the title compound as a yellow solid. NMR: 8.52 (m, 1H), 8.12 (m, 2H), 7.94 (d, 1H), 7.61 (m, 2H), 2.92 (s, 3H).

Workup

  1. customthe temperature below −10° C
  2. stirringstirred for 16 h
  3. extractionextracted into DCM
  4. washThe organic layers were further washed with water
  5. customdried
  6. custompurified by chromatography (eluent—50% DCM /isohexane)

Sources & evidence

ORD record
ord-c0e337109ee04b26b3b0818dc5585839
Source dataset
uspto-grants-2005_11
Patent number
US06967216B2

Reaction notes

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