Hydrochloric Acid → 5-Bromo-2-[(4-fluorobenzyl)oxy]benzoic acid

HRID 1623708Notes

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][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].Cl>O1CCCC1.O>[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

Conditions

Temperature: 70 °C

Procedure

Solid LiOH (0.23 g, 9.58 mmol) was added to a stirred solution of (4-fluorophenyl)methyl 5-bromo-2-{[(4-fluorophenyl)methyl]oxy}benzoate (may be prepared as described in Description 86; 1 g, 1.92 mmol) in tetrahydrofuran (30 ml) and water (10 ml) in air at room temperature. The reaction mixture was stirred at 70° C. overnight. After cooling to room temperature, the solvent was removed to obtain a solid, which was dissolved in water (20 ml) and stirred in an ice-water bath. 1N HCl (aq) was added to adjust the pH to 4. The solid was filtered, and dried in vacuo to yield the title compound as a grey solid. 674 mg.

Workup

temperatureAfter cooling to room temperature
customthe solvent was removed
customto obtain a solid, which
stirringstirred in an ice-water bath
filtrationThe solid was filtered
customdried in vacuo

Sources & evidence

ORD record: ord-f08351142d56476e9d6d3fdab8d89caa
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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