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

HRID 1623648
Notes
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Reaction equation

HRID 1623648 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][CH:26]=[CH:25][C:24]=2[Cl:29])=[C:8]([CH:20]=1)[C:9]([O:11]CC1C=CC=CC=1Cl)=[O:10]>O.C1COCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])=[C:8]([CH:20]=1)[C:9]([OH:11])=[O:10]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67107474HCID 67107474, compound

Product 1

HCID 87070765-Bromo-2-[(2-chlorobenzyl)oxy]benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A solution of lithium hydroxide (468 mg, 11.16 mmol) in water (25 m) was added dropwise to a stirred solution of (2-chlorophenyl)methyl 5-bromo-2-{[(2-chlorophenyl)methyl]oxy}benzoate (may be prepared as described in Description 27; 520 mg, 1.12 mmol) in THF (25 ml) over 1 min. The reaction mixture was stirred at 20° C. for 16 hours. The organic phase was evaporated and the aqueous phase (25 ml) was adjusted to pH 2 with 2M hydrochloric acid (1 ml) and was extracted by ethyl acetate (3×20 ml). The organic phase was evaporated in vacuo to yield the title compound as a light yellow solid. 350 mg.

Workup

  1. customThe organic phase was evaporated
  2. extractionwas extracted by ethyl acetate (3×20 ml)
  3. customThe organic phase was evaporated in vacuo

Sources & evidence

ORD record
ord-f8ff005f7298447b89adeb23e8bd7e85
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08778939B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes