Hydrochloric Acid → 5-Bromo-2-{[(2,4-difluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)benzoic acid

HRID 2204689Notes

Reaction equation

[Br:1][C:2]1[C:3]([CH2:30][N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[CH:4][C:5]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2[F:29])=[C:6]([CH:19]=1)[C:7]([O:9]CC1C=CC(F)=CC=1F)=[O:8].[OH-].[Li+].O.Cl>O1CCCC1>[Br:1][C:2]1[C:3]([CH2:30][N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[CH:4][C:5]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2[F:29])=[C:6]([CH:19]=1)[C:7]([OH:9])=[O:8]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (2,4-difluorophenyl)methyl 5-bromo-2-{[(2,4-difluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)benzoate (may be prepared as described in Description 21; 833 mg, 1.466 mmol) in tetrahydrofuran (4 ml) was added lithium hydroxide (211 mg, 8.79 mmol) and water (1 ml). The mixture was heated at 50° C. for 4 hours, cooled and neutralised with 2M hydrochloric acid (3.66 ml, 7.33 mmol). The solvent was removed in vacuo to yield the title compound as a white solid. 648 mg.

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-49a559b4570848f08d1ba08d185cf120
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365551B2

Reaction notes

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