[2-Chloro-6-(trifluoromethyl)pyridin-3-yl]methanol → 2-Chloro-6-(trifluoromethyl)pyridine-3-carbaldehyde

HRID 623317Notes

Reaction equation

HRID 623317 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[C:4]([C:10]([F:13])([F:12])[F:11])[N:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[Cl:1][C:2]1[N:3]=[C:4]([C:10]([F:13])([F:11])[F:12])[CH:5]=[CH:6][C:7]=1[CH:8]=[O:9]

Participants

4

Reactant 2

HCID 53256696[2-Chloro-6-(trifluoromethyl)pyridin-3-yl]methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 467399062-Chloro-6-(trifluoromethyl)pyridine-3-carbaldehydeYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [2-chloro-6-(trifluoromethyl)pyridin-3-yl]methanol (Int-16) (80.0 g, 1.0 eq.) in dichloromethane (700 ml) was added pyridinium chlorochromate (160.0 g, 2.0 eq), silicium dioxide (240 g) at room temperature and stirred for 4 h. The progress of the reaction was monitored by TLC. After completion of reaction, reaction mixture was filtered through silica gel bed and washed the bed with excess 90% ethyl acetate in pet ether and filtrate was concentrated under reduced pressure to get crude 2-chloro-6-(trifluoromethyl)nicotinaldehyde (Int-17) as yellow liquid (70.0 g, 88.3%). GC-MS: m/z 209 ([M]).

Workup

  1. customAfter completion of reaction, reaction mixture
  2. filtrationwas filtered through silica gel bed
  3. washwashed the bed with excess 90% ethyl acetate in pet ether and filtrate
  4. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-1031ba65d9544db5a39cfaecf3b4391c
Source dataset
uspto-grants-2016_04
Patent number
US09301526B2

Reaction notes

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