Lithium Hydroxide → 5-Bromo-2-[(4-fluorobenzyl)oxy]benzoic acid

HRID 1623709Notes

Reaction equation

HRID 1623709 reaction equation
[OH-].[Li+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[C:8]([CH:20]=1)[C:9]([O:11]CC1C=CC(F)=CC=1)=[O:10]>O.O1CCCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)=[C:8]([CH:20]=1)[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67107744(4-Fluorophenyl)methyl 5-bromo-2-{[(4-fluorophenyl)methyl]oxy}benzoate

Product 1

HCID 87068895-Bromo-2-[(4-fluorobenzyl)oxy]benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (0.43 g, 18.14 mmol) was added to a solution of (4-fluorophenyl)methyl 5-bromo-2-{[(4-fluorophenyl)methyl]oxy}benzoate (may be prepared as described in Description 86) (2.62 g, 6.05 mmol) in water (5 ml) and tetrahydrofuran (20 ml). The mixture was stirred overnight and the solvent removed in vacuo. The residue was redissolved in water (30 ml) and acidified to pH=2 using 1N HCl and then extracted with ethyl acetate (3×25 ml). The combined organic layers were dried (MgSO4) and the solvent removed in vacuo to yield the titled compound as a white solid. 1.97 g.

Workup

  1. customthe solvent removed in vacuo
  2. dissolutionThe residue was redissolved in water (30 ml)
  3. extractionextracted with ethyl acetate (3×25 ml)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-4097d200e93741f183d0e7440778c941
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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