Dimethylformamide → Methyl 4-fluorosalicylate

HRID 1024415Notes

Reaction equation

HRID 1024415 reaction equation
[CH3:1]N(C=O)C.[F:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([OH:16])[CH:8]=1.C(=O)([O-])O.[K+].IC>O>[F:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([O:13][CH3:1])=[O:12])=[C:9]([OH:16])[CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 676614-Fluorosalicylic acidHCID 516893Potassium Bicarbonate

Product 1

HCID 2775386Methyl 4-fluorosalicylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.1 50 ml of DMF are added under argon to 6.0 g of 4-fluoro-2-hydroxybenzoic acid and 4.52 g of potassium hydrogencarbonate, and the mixture is stirred for 10 minutes. 3.05 ml of iodomethane are added dropwise, and the mixture is stirred at 40° for 3 hours. The mixture is poured into 150 ml of water and subjected to conventional work-up, giving 6.48 g of methyl 4-fluoro-2-hydroxybenzoate (“1a”).

Workup

  1. stirringthe mixture is stirred at 40° for 3 hours

Sources & evidence

ORD record
ord-1d9fa81cc0e84650a0c66a1d3853be03
Source dataset
uspto-grants-2014_05
Patent number
US08722903B2

Reaction notes

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