3-Fluoro-2-hydroxybenzoic acid → Methyl 3-fluoro-2-hydroxybenzoate

HRID 1390922

Reaction equation

HRID 1390922 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[OH:11].B(F)(F)F.CO.[C:18](=O)(O)[O-].[Na+]>CO>[CH3:18][O:6][C:5](=[O:7])[C:4]1[C:3](=[C:2]([F:1])[CH:10]=[CH:9][CH:8]=1)[OH:11]

Participants

5

Reactant 3

HCID 2687243-Fluoro-2-hydroxybenzoic acidHCID 516892Sodium BicarbonateHCID 11062313373-57-9

Product 1

HCID 573875Methyl 3-fluoro-2-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 15.6 g (0.10 mole) portion of 3-fluorosalicylic acid was dissolved in a 100 ml portion of absolute methanol. A 22 ml portion of borontrifluoride-methanol reagent (2 equivalents, 51% BF3) was added and the reaction allowed to reflux for about six hours. The reaction mixture was cooled and added carefully to a saturated solution of sodium bicarbonate. The resulting mixture was then extracted with ether, the ether layer dried over magnesium sulfate and evaporated in vacuo. The oil obtained was crystallized from methanol. The methyl-3-fluorosalicylate obtained had a melting point of 94°-5° C.

Workup

  1. temperatureto reflux for about six hours
  2. temperatureThe reaction mixture was cooled
  3. extractionThe resulting mixture was then extracted with ether
  4. dry with materialthe ether layer dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe oil obtained
  7. customwas crystallized from methanol

Sources & evidence

ORD record
ord-67d48203d25e4475b44bc5781c643097
Source dataset
uspto-grants-1979_02
Patent number
US04140769

Linked notes

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