1,4-Dibromobenzene → HCID 68193231, compound

HRID 1626807Notes

Reaction equation

HRID 1626807 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.CON(C)[C:23](=[O:32])[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[N:26][CH:25]=1>O1CCCC1.O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:23]([C:24]2[CH:25]=[N:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)=[O:32])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 78041,4-DibromobenzeneHCID 8058HexaneHCID 45867410HCID 45867410, compoundHCID 178418339Butyllithium

Product 1

HCID 68193231HCID 68193231, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1,4-Dibromobenzene (6.5 g, 27 mmol) was dissolved in tetrahydrofuran (120 mL), and a solution of n-butyllithium in hexane (2.6 M, 10 mL, 27 mmol) was added at −78° C., followed by stirring at the same temperature for 30 minutes. A solution of N,6-dimethoxy-N-methylnicotinamide (2.7 g, 14 mmol) in tetrahydrofuran (20 mL) was added to the reaction solution, followed by stirring at −78° C. for further 30 minutes. Water was added to the reaction solution, followed by extraction with ethyl acetate, and subsequently the organic layer was concentrated under reduced pressure. The resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.50 (hexane/ethyl acetate=10/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (2.8 g, 9.4 mmol) as a white solid (yield 69%).

Workup

  1. stirringby stirring at −78° C. for further 30 minutes
  2. extractionfollowed by extraction with ethyl acetate
  3. concentrationsubsequently the organic layer was concentrated under reduced pressure
  4. customThe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  5. concentrationa fraction corresponding to the Rf value=0.50 (hexane/ethyl acetate=10/1) by thin layer chromatography was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0f5c82a0e6a8470cb865e8db4319fb3f
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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