Thionyl Chloride → Methyl 2-amino-6-fluorobenzoate

HRID 1294563Notes

Reaction equation

HRID 1294563 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[C:16]([O-])(O)=O.[Na+]>CO.O1CCOCC1>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([O:6][CH3:16])=[O:5]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 5211422-Amino-6-fluorobenzoic acid

Product 1

HCID 2818492Methyl 2-amino-6-fluorobenzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

5 g (31.6 mmol) 2-amino-6-fluorobenzoic acid are dissolved in 50 ml of methanol and combined with 7.9 ml (31.6 mmol) of a 4 M solution of HCL in 1,4-dioxane and stirred for 10 min. at ambient temperature. The reaction mixture is combined dropwise with 3.45 ml (47.4 mmol) thionyl chloride and refluxed for 3 h. Then the reaction mixture is neutralised with 150 ml of a saturated, aqueous NaHCO3 solution and extracted four times with 100 ml of ethyl acetate. The organic phase is dried with MgSO4 and the solvent is eliminated in vacuo.

Workup

  1. temperaturerefluxed for 3 h
  2. extractionextracted four times with 100 ml of ethyl acetate
  3. dry with materialThe organic phase is dried with MgSO4

Sources & evidence

ORD record
ord-0146e07931354bd3a1090c9b152f207e
Source dataset
uspto-grants-2007_07
Patent number
US07241769B2

Reaction notes

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