2-Bromo-1-(3,4-dichlorophenyl)ethanone → HCID 178477975, compound

HRID 276771

Reaction equation

HRID 276771 reaction equation
C[Si](C)(C)[N-:3][Si](C)(C)C.[Li+].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][N:13]=1.C(=O)(O)[O-].[Na+].[Cl:25][C:26]1[CH:27]=[C:28]([CH:33]=[CH:34][C:35]=1[Cl:36])[C:29](=O)[CH2:30]Br>C1COCC1.C(Cl)(Cl)Cl.O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[NH:3][CH:30]=[C:29]([C:28]3[CH:33]=[CH:34][C:35]([Cl:36])=[C:26]([Cl:25])[CH:27]=3)[N:19]=2)=[CH:14][N:13]=1

Participants

8

Reactant 4

HCID 2447512-Bromo-1-(3,4-dichlorophenyl)ethanoneHCID 516892Sodium BicarbonateHCID 2733832Lithium HexamethyldisilazideHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 178477975HCID 178477975, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium hexamethyldisilazide (41.5 mL of a 1.0 M solution in THF) was added to a solution of 2-chloro-5-cyanopyridine (5.24 g) in THF (10 mL). The resultant mixture was stirred at room temperature for 30 min, and then 13 mL saturated aqueous sodium bicarbonate and 5 mL water were added to the reaction mixture. A solution of 3,4-dichlorophenacyl bromide (10.13 g) in chloroform (150 mL) was added in two portions approximately 15 min apart. The resultant mixture was stirred for 72 hours, and the reaction mixture was filtered. The filter cake was triturated with dichloromethane (50 mL) to provide 2-Chloro-5-[4-(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridine (10.46 g). MS m/z 324 (M+), 326 (M++2).

Workup

  1. filtrationthe reaction mixture was filtered
  2. customThe filter cake was triturated with dichloromethane (50 mL)

Sources & evidence

ORD record
ord-ee9b6e165ef34b6fb9cf15324b2925e1
Source dataset
uspto-grants-2002_03
Patent number
US06355635B1

Linked notes

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