Water → HCID 16639482, compound

HRID 2104937Notes

Reaction equation

HRID 2104937 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:9]=[C:10]2[C:15](=O)[O:14][C:12](=[O:13])[C:11]2=[CH:17][C:18]=1[F:19].[OH-].[Na+].O>C1COCC1>[F:7][C:8]1[CH:9]=[C:10]([CH2:15][OH:14])[C:11]([CH2:12][OH:13])=[CH:17][C:18]=1[F:19]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 6397454,5-Difluorophthalic AnhydrideHCID 21226445Aluminium lithium hydride

Product 1

HCID 16639482HCID 16639482, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of LiAlH4 (1M in tetrahydrofuran) (11 ml, 11.0 mmol, 2.0 molar equivalents) cooled to −78° C. was added dropwise a solution of 4,5-difluorophtalic anhydrid (1.0 g, 5.4 mmol, 1 molar equivalent) in THF (5 ml). The reaction mixture was allowed to warm up to room temperature and then stirred at 70° C. for 2 hours. To this resulting solution cooled to 0° C. was added a 2M sodium hydroxide solution (5 ml) followed by cold water (5 ml) and THF (10 ml). The reaction mixture was then further extracted with THF (3 times 20 ml). The organic fractions were combined, washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuum to give a light yellow solid. Purification by recrystallisation from acetone/hexane gave the title compound as light yellow needles (0.8 g, 85%). 1H NMR (300.13 MHz, DMSO) δ(ppm) 4.47 (d, J=5.30, 4H) 5.26 (t, J=5.30 Hz, 2H) 7.36 (t, J=10.10 Hz, 2H). 19F NMR (282.38 MHz, DMSO) δ(ppm) −142.27 (s).

Workup

  1. temperatureTo this resulting solution cooled to 0° C.
  2. extractionThe reaction mixture was then further extracted with THF (3 times 20 ml)
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customto give a light yellow solid
  8. customPurification
  9. customby recrystallisation from acetone/hexane

Sources & evidence

ORD record
ord-5b3cc74c5a6d49098536c43747f59c6b
Source dataset
uspto-grants-2009_08
Patent number
US07576208B2

Reaction notes

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