Hydrochloric Acid → HCID 8706995, compound

HRID 1623704Notes

Reaction equation

HRID 1623704 reaction equation
[Li+].[OH-].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=2)=[C:8]([CH:20]=1)[C:9]([O:11]CC1C=CC=C(F)C=1)=[O:10].Cl>O1CCCC1.O.C(OCC)(=O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=2)=[C:8]([CH:20]=1)[C:9]([OH:11])=[O:10]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67106781HCID 67106781, compound

Product 1

HCID 8706995HCID 8706995, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
71 °C

Procedure

Solid LiOH (0.50 g, 20.95 mmol) was added in one charge to a stirred solution of (3-fluorophenyl)methyl 5-bromo-2-{[(3-fluorophenyl)methyl]oxy}benzoate (may be prepared as described in Description 82; 1.65 g, 3.81 mmol) in tetrahydrofuran (15 ml) and water (5 ml) in air at 20° C. The reaction mixture was stirred at 71° C. for 16 h. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (200 ml). 10% Aqueous HCl was added to the mixture to adjust pH to 2. The organic phase was isolated, washed with brine, dried over Na2SO4, and concentrated to yield the title compound as a white solid. 1.5 g.

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe organic phase was isolated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4b58f5af1e854b5a9c77ff2e43c6b18f
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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