Water → HCID 86598309, compound

HRID 2101203Notes

Reaction equation

HRID 2101203 reaction equation
[F:1][C:2]([F:24])([F:23])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[C:18]1N=CNN=1.C1COCC1.[Li+].[OH-:31].[OH2:32]>>[F:1][C:2]([F:24])([F:23])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[C:18]([OH:32])=[O:31]

Participants

5

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 178505561HCID 178505561, compound

Product 1

HCID 86598309HCID 86598309, compound

Procedure

To a solution of 0.75 g (2.29 mol) of Methyl 1-3-((2-trifluoroethoxy)phenyl)-4-fluorobenzoate (Example 8, Step B) in 11.5 Ml of a 3:1 mixture of THF:water was added 0.164 g (6.86 mmol) of LiOH and the reaction mixture was stirred at RT for 18 hr. The reaction mixture was concentrated and the Ph was adjusted to Ph=2 with 1N HCl solution. The mixture was extracted with EtOAc and the combine organic fractions were washed with brine, dried over MgSO4, filtered and the filtrate was concentrated to give the title compound which was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionThe mixture was extracted with EtOAc
  3. washthe combine organic fractions were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b5bdf54da1a942ada5af7959f43ef978
Source dataset
uspto-grants-2009_08
Patent number
US07572822B2

Reaction notes

Loading…