3,4-Difluoro-1,2-benzenedicarboxylic acid → HCID 59314172, compound

HRID 1047947Notes

Reaction equation

HRID 1047947 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[C:16]([F:17])=[CH:15][CH:14]=[C:10]([C:11](O)=[O:12])[C:9]=1[C:18](O)=[O:19]>C1COCC1>[F:7][C:8]1[C:16]([F:17])=[CH:15][CH:14]=[C:10]([CH2:11][OH:12])[C:9]=1[CH2:18][OH:19]

Participants

4

Reactant 2

HCID 183537993,4-Difluoro-1,2-benzenedicarboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 59314172HCID 59314172, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LAH (6.2 g, 0.163 mol) in dry THF (100 ml) is added a solution of compound 3,4-difluoro-phthalic acid (15 g, 0.074 mol) in THF (75 mL), drop wise at 0° C. The resulting mixture is refluxed for 3 h. After 3 h the reaction mixture is cooled and quenched with saturated Na2SO4 solution. Then the reaction mass is filtered through a pad of celite and the bed is washed thoroughly with MeOH. The combined filtrate is concentrated to yield a crude product that is purified by column chromatography (silica, 5% MeOH in DCM). Combination of appropriate fractions followed by removal of the solvent yields white solid (7 g, 54.2%).

Workup

  1. customdrop wise at 0° C
  2. temperatureThe resulting mixture is refluxed for 3 h
  3. temperatureAfter 3 h the reaction mixture is cooled
  4. customquenched with saturated Na2SO4 solution
  5. filtrationThen the reaction mass is filtered through a pad of celite
  6. washthe bed is washed thoroughly with MeOH
  7. concentrationThe combined filtrate is concentrated
  8. customto yield a crude product that
  9. customis purified by column chromatography (silica, 5% MeOH in DCM)
  10. customCombination of appropriate fractions followed by removal of the solvent

Sources & evidence

ORD record
ord-a6cf17d367a946f2a945dd567d47669d
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

Loading…