Phenyltriethylammonium tribromide → 2-Bromo-1-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethanone

HRID 56062Notes

Reaction equation

HRID 56062 reaction equation
[Cl:1][C:2]1[C:3]([C:14](=[O:16])[CH3:15])=[N:4][CH:5]=[C:6]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[CH:7]=1.[Br-:17].[Br-].[Br-].C([N+](CC)(CC)C1C=CC=CC=1)C.C([N+](C1C=CC=CC=1)(CC)CC)C.C([N+](C1C=CC=CC=1)(CC)CC)C>O1CCCC1>[Br:17][CH2:15][C:14]([C:3]1[C:2]([Cl:1])=[CH:7][C:6]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[CH:5][N:4]=1)=[O:16]

Participants

4

Reactant 2

HCID 86591495Phenyltriethylammonium tribromideHCID 1180716091-[3-Chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethanone

Product 1

HCID 1180715932-Bromo-1-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethanoneYield 189.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1.1 g of 1-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethanone in 20 ml of tetrahydrofuran, 1.6 g of triethylphenylammonium tribromide was added, and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the precipitated solid was filtered off through celite, and the solvent was evaporated under reduced pressure to obtain 1.3 g of the desired crude product as a pale yellow oil. The oil was used in the next step without further purification.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe precipitated solid was filtered off through celite
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e195ab8fb10d44299937e8e49e849d83
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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