2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 10087537, compound

HRID 1956960Notes

Reaction equation

HRID 1956960 reaction equation
[Br:1][C:2]1[CH:11]([CH3:12])[CH2:10][C:9]2[C:4](=[CH:5][C:6]([O:18][CH3:19])=[C:7]([O:16][CH3:17])[C:8]=2[CH:13]([CH3:15])[CH3:14])[CH:3]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([C:8]([CH:13]([CH3:14])[CH3:15])=[C:7]([O:16][CH3:17])[C:6]([O:18][CH3:19])=[CH:5]2)=[CH:10][C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 9996412HCID 9996412, compound

Product 1

HCID 10087537HCID 10087537, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Compound 13 (3.50 g, 10.8 mmol) was dissolved in 25 mL of benzene and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (2.45 g, 10.8 mmol) was added slowly with stirring and stirring was continued for 2 h. The reaction mixture was filtered through a short column of silica and eluted with dichloromethane. The solvent was evaporated and the product was crystallized from petroleum ether to give 3.21 g (9.93 mmol, 92%) of 14 as colorless crystals: mp 62°-63° C.; 1H NMR δ 1.51 (d, J-7.2 Hz, 6 H), 2.56 (s, 3 H), 3.90 (s, 3 H), 3.96 (s, 3H), 3.97 (m, 1 H), 6.94 (s, 1 H), 7.92 (s, 1 H), 7.96 (s, 1 H). Anal. (C16H19 BrO2) C,H.

Workup

  1. stirringstirring
  2. filtrationThe reaction mixture was filtered through a short column of silica
  3. washeluted with dichloromethane
  4. customThe solvent was evaporated
  5. customthe product was crystallized from petroleum ether

Sources & evidence

ORD record
ord-3b7a20e2f25c473095ac2cbad54f8cba
Source dataset
uspto-grants-1998_07
Patent number
US05780675

Reaction notes

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