p-Bromochlorobenzene → (4-Chlorophenyl)(6-chloro-3-pyridinyl)methanone

HRID 1799162Notes

Reaction equation

HRID 1799162 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][CH:3]=1.[Li]CCCC.[Cl:14][C:15]1[CH:26]=[CH:25][C:18]([C:19](N(OC)C)=[O:20])=[CH:17][N:16]=1>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:19]([C:18]2[CH:17]=[N:16][C:15]([Cl:14])=[CH:26][CH:25]=2)=[O:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7806p-BromochlorobenzeneHCID 114355976-Chloro-N-methoxy-N-methylnicotinamideHCID 178418339Butyllithium

Product 1

HCID 20145731(4-Chlorophenyl)(6-chloro-3-pyridinyl)methanoneYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-chlorobromobenzene (33.88 g, 177 mmol) in THF (200 mL), a solution of BuLi (118 mL, 142 mmol, 1.2 M solution in hexane) was added at −78° C. The mixture was stirred for 1 h and a solution of compound A (23.6 g, 118 mmol) in THF (100 mL) was added to it dropwise. The mixture was stirred for additional 1 h, quenched with saturated NH4Cl solution and extracted with ethyl acetate (300 mL). The organic layer was dried (Na2SO4), filtered and evaporated. The crude product was purified using column chromatography to obtain 23.4 g (79%) of compound B as light yellow solid.

Workup

  1. stirringThe mixture was stirred for additional 1 h
  2. customquenched with saturated NH4Cl solution
  3. extractionextracted with ethyl acetate (300 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-906959fc0be64860a6ec10f57ce7f813
Source dataset
uspto-grants-2013_01
Patent number
US08343996B2

Reaction notes

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