6-Fluoronicotinic Acid → 1-(6-Fluoropyridin-3-yl)ethan-1-one

HRID 1194656Notes

Reaction equation

HRID 1194656 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=O)=[CH:4][N:3]=1.[CH3:11][Li]>CCOCC>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[N:3][CH:4]=1)(=[O:10])[CH3:11]

Participants

4

Reactant 2

HCID 2428196-Fluoronicotinic AcidHCID 178418348HCID 178418348, compound

Product 1

HCID 130903391-(6-Fluoropyridin-3-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of 20 gm. (142 mmoles) of 2-fluoro-5-pyridinecarboxylic acid (J. Am. Chem. Soc., 71, 1125 (1949)) in 750 ml of ether, stirred and cooled in ice, was added 225 ml of 1.6M methyl lithium (360 mmoles) in ether over 1 hour. The reaction was stirred for an additional 2 hours, then 300 ml of ice water was added. The aqueous layer was washed with 2×100 ml fresh ether, acidified and extracted with ether to give 5.0 gm. (25%) of unreacted starting acid.

Workup

  1. additionTo a suspension of 20 gm
  2. temperaturecooled in ice
  3. washThe aqueous layer was washed with 2×100 ml fresh ether
  4. extractionextracted with ether
  5. customto give 5.0 gm

Sources & evidence

ORD record
ord-1d4455da1c9546e8b89847ebc1f02ff6
Source dataset
uspto-grants-1989_03
Patent number
US04816457

Reaction notes

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