Toluene → 5-Fluoropyridine-2-carboxaldehyde

HRID 1791355Notes

Reaction equation

HRID 1791355 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][N:7]=1)=O)C.C1(C)C=CC=CC=1>ClCCl.CC(C[AlH]CC(C)C)C>[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH:4]=[O:3])=[N:7][CH:8]=1

Participants

5

Reactant 2

HCID 1140TolueneHCID 10986675Ethyl 5-fluoropyridine-2-carboxylate

Product 1

HCID 103516975-Fluoropyridine-2-carboxaldehydeYield 56.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14487Diisobutylaluminum hydrideSolvent

Procedure

To 5-fluoro-pyridine-2-carboxylic acid ethyl ester (94 mg, 0.556 mmol) in dichloromethane (4.0 mL), 1 M DIBAL in toluene (1.23 mL, 1.23 mmol) was added at room temperature and the mixture was stirred for 30 min. The reaction mixture was quenched with 2 M sodium carbonate and extracted with dichloromethane. The dichloromethane was dried and concentrated to give 39 mg (54.7%) of crude 5-fluoro-pyridine-2-carbaldehyde which could be used for the next step reaction without further purification. GC-MS (M+): 125

Workup

  1. customThe reaction mixture was quenched with 2 M sodium carbonate
  2. extractionextracted with dichloromethane
  3. dry with materialThe dichloromethane was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f4e88c7a4f2f4535a5b7fe669b0b17f4
Source dataset
uspto-grants-2006_07
Patent number
US07074809B2

Reaction notes

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