Ammonium Chloride → (6-Bromo-4-methylpyridin-3-yl)(2,3,6-trifluorophenyl)methanol

HRID 1641697Notes

Reaction equation

HRID 1641697 reaction equation
C([Li])CCC.[Br:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10](Br)=[CH:9][N:8]=1.[F:15][C:16]1[C:23]([F:24])=[CH:22][CH:21]=[C:20]([F:25])[C:17]=1[CH:18]=[O:19].[Cl-].[NH4+]>C(OCC)C.CCCCCC>[Br:6][C:7]1[N:8]=[CH:9][C:10]([CH:18]([C:17]2[C:20]([F:25])=[CH:21][CH:22]=[C:23]([F:24])[C:16]=2[F:15])[OH:19])=[C:11]([CH3:13])[CH:12]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 5178452,3,6-TrifluorobenzaldehydeHCID 27344292,5-Dibromo-4-methylpyridineHCID 178418339Butyllithium

Product 1

HCID 86631150(6-Bromo-4-methylpyridin-3-yl)(2,3,6-trifluorophenyl)methanolYield 81.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

A hexane solution of n-butyllithium (1.54 M, 12.2 ml, 18.7 mmol) was added to a solution of 2,5-dibromo-4-methylpyridine (4.27 g, 17.0 mmol) in diethyl ether (200 ml) in an argon atmosphere at −78° C. After stirring the reaction mixture for 30 minutes, 2,3,6-trifluorobenzaldehyde (1.99 ml, 17.0 mmol) was added thereto. After stirring for 30 minutes at the same temperature, saturated aqueous ammonium chloride was added to the mixture at room temperature. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was subjected to flash silica gel chromatography. The fraction obtained from an elution with hexane:ethyl acetate=4:1 was concentrated under reduced pressure to obtain the title compound (4.60 g, 13.9 mmol, 81%) as a pale yellow solid.

Workup

  1. additionwas added to the mixture at room temperature
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe fraction obtained from an elution with hexane
  6. concentrationethyl acetate=4:1 was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e9ca1cc13c424495b5ada26415834050
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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