Water → HCID 62196689, compound

HRID 1623722Notes

Reaction equation

HRID 1623722 reaction equation
[OH-].[Li+].O.[Br:4][C:5]1[CH:6]=[CH:7][C:8]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[F:32])=[C:9]([CH:22]=1)[C:10]([O:12]CC1C=CC(F)=CC=1F)=[O:11]>O1CCCC1>[Br:4][C:5]1[CH:6]=[CH:7][C:8]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[F:32])=[C:9]([CH:22]=1)[C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 67107475HCID 67107475, compound

Product 1

HCID 62196689HCID 62196689, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (0.83 g, 34.5 mmol) and water (50 ml) were added to a solution of (2,4-difluorophenyl)methyl 5-bromo-2-{[(2,4-difluorophenyl)methyl]oxy}benzoate (may be prepared by Description 102; 5.39 g, 11.49 mmol) in tetrahydrofuran (200 ml). The mixture was heated to reflux for 2 hrs. The tetrahydrofuran was then removed on a buchi and the aqueous mixture was acidified to pH=1 using 2M aqueous HCl. The solid formed was filtered off, washed with water (2×50 ml) and dried in air under vacuum. The solid was triturated with diethyl ether to give a white solid. 3.1 g.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hrs
  3. customThe tetrahydrofuran was then removed on a buchi
  4. customThe solid formed
  5. filtrationwas filtered off
  6. washwashed with water (2×50 ml)
  7. customdried in air under vacuum
  8. customThe solid was triturated with diethyl ether
  9. customto give a white solid

Sources & evidence

ORD record
ord-c67950ed7e214228ae81d30b94e11cd0
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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