2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 57592516, compound

HRID 1784394Notes

Reaction equation

HRID 1784394 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([Br:7])[CH:6]=1.C([Li])CCC.[Cl:13][C:14]1[N:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(OCC)C.C(OCC)(=O)C>[Br:7][C:5]1[CH:6]=[C:2]([C:16]2[CH:17]=[CH:18][N:19]=[C:14]([Cl:13])[N:15]=2)[S:3][CH:4]=1

Participants

7

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 744042-ChloropyrimidineHCID 2724560Thiophene, 2,4-dibromo-HCID 178418339Butyllithium

Product 1

HCID 57592516HCID 57592516, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled (−78° C.) solution of 2,4-dibromothiophene (1 g, 4.13 mmol) in diethylether (30 ml) was added n-butyl lithium (2.5M in Hexanes, 4.55 mmol, 1.82 ml). The solution was maintained at this temperature for 1 hour before the addition of 2-chloropyrimidine (0.47 g, 4.13 mmol) in a single portion. The mixture was maintained at −78° C. for a further 1.5 hours before being allowed to warm up to room temperature. Ethyl acetate (20 ml) was added followed by DDQ (0.94 g, 4.13 mmol). The reaction was stirred for a further 30 minutes before being concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2) (7:3—Hexanes:EtOAc) to give the desired product (0.42 g, 37%) as a pale yellow solid which corresponded to the title compound. m/z (LC-MSW, ESP):275 [M+H]+, R/T=4.72 mins.

Workup

  1. temperatureto warm up to room temperature
  2. concentrationbefore being concentrated in vacuo
  3. customThe crude residue was purified by flash chromatography (SiO2) (7:3—Hexanes:EtOAc)

Sources & evidence

ORD record
ord-29590f2670a04d1d8482a49543b7c71c
Source dataset
uspto-grants-2009_03
Patent number
US07504397B2

Reaction notes

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