Phenyltrimethylammonium bromide dibromide → 2-Bromo-1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethanone

HRID 655927Notes

Reaction equation

HRID 655927 reaction equation
[Cl:1][C:2]1[C:3]([C:12](=[O:14])[CH3:13])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[Br-:15].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>O1CCCC1>[Br:15][CH2:13][C:12]([C:3]1[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:11])([F:9])[F:10])=[CH:5][N:4]=1)=[O:14]

Participants

4

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 217121361-(3-Chloro-5-trifluoromethyl-pyridin-2-yl)-ethanone

Product 1

HCID 860575962-Bromo-1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 16.6 g (0.074 mol) of 1-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethanone in 150 ml of dry tetrahydrofuran, were added portionwise at room temperature 27.8 g (0.074 mol) of phenyltrimethylammonium tribromide. The solution was stirred for 3-hours at room temperature. The formed solid was removed by filtration and the mother liquors were concentrated under vacuum. The resulting orange oil (32.7 g) was purified by flash chromatography on silica gel (eluent: heptane/dichloromethane 3:1) to give 2-bromo-1-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethanone: 10.4 g (46%) as a yellow oil.

Workup

  1. customThe formed solid was removed by filtration
  2. concentrationthe mother liquors were concentrated under vacuum
  3. customThe resulting orange oil (32.7 g) was purified by flash chromatography on silica gel (eluent: heptane/dichloromethane 3:1)

Sources & evidence

ORD record
ord-c647c2a15b3d4f6ca353c808ff60e594
Source dataset
uspto-grants-2011_12
Patent number
US08071627B2

Reaction notes

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