Sodium Carbonate → HCID 87158388, compound

HRID 2206907Notes

Reaction equation

HRID 2206907 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH2:12][CH2:11][C:10]([C:17]3[CH:22]=[C:21]([Cl:23])[C:20]([Cl:24])=[C:19]([Cl:25])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[CH2:9]2)[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[Br:32]Br>ClCCl>[Br:32][C:7]1[C:2]([CH3:1])=[N:3][C:4]([N:8]2[CH2:12][CH2:11][C:10]([C:17]3[CH:18]=[C:19]([Cl:25])[C:20]([Cl:24])=[C:21]([Cl:23])[CH:22]=3)([C:13]([F:14])([F:16])[F:15])[CH2:9]2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24408BromineHCID 87158436HCID 87158436, compound

Product 1

HCID 87158388HCID 87158388, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a dichloromethane (200 ml) solution of 2-methyl-6-[3-(3,4,5-trichlorophenyl)-3-(trifluoro-methyl)pyrrolidin-1-yl]pyridine (3.4 g), an aqueous solution (100 ml) of sodium carbonate (1.2 g) was added. Under ice cooling, a dichloromethane solution of bromine (1.4 g) was added dropwise. Upon the completion of the dropwise addition, the stirring was continued for 1 hour at 0° C. The dichloromethane layer was separated and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography to obtain 3-bromo-2-methyl-6-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]pyridine (3.3 g).

Workup

  1. additionUpon the completion of the dropwise addition
  2. customThe dichloromethane layer was separated
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1afbc6a50e844bd0851b2b67898ea01c
Source dataset
uspto-grants-2016_06
Patent number
US09375000B2

Reaction notes

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