Hydrochloric Acid → HCID 67107253, compound

HRID 1623713Notes

Reaction equation

HRID 1623713 reaction equation
O.[OH-].[Li+].[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])=[C:27]([F:32])[CH:26]=2)=[C:9]([CH:22]=1)[C:10]([O:12]CC1C=CC(F)=C(F)C=1)=[O:11].Cl>O1CCCC1.C(OCC)(=O)C>[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])=[C:27]([F:32])[CH:26]=2)=[C:9]([CH:22]=1)[C:10]([OH:12])=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 67106784HCID 67106784, compound

Product 1

HCID 67107253HCID 67107253, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Water (50 ml) and lithium hydroxide (0.60 g, 24.93 mmol) were added to a solution of (3,4-difluorophenyl)methyl 5-bromo-2-{[(3,4-difluorophenyl)methyl]oxy}benzoate (may be prepared by Description 88; 3.9 g, 8.31 mmol) in tetrahydrofuran (150 ml). The mixture was heated to reflux for 2 hours. The mixture was allowed to cool and diluted with ethyl acetate (200 ml) and this mixture was then acidified to pH=1 using 2M aqueous HCl. The organics were separated and the aqueous layer was extracted with ethyl acetate (100 ml). The organics were combined, dried (MgSO4) and evaporated under reduced pressure to yield the title compound as a white solid. 2.9 g. The residue contains some benzyl alcohol.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureto cool
  4. customThe organics were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (100 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8ec938da7ede4e8baee1b6034f2d9ae2
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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