Lithium Hydroxide → 5-bromo-2-[(2-chlorobenzyl)oxy]benzoic acid
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]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- customThe organic phase was evaporated
- extractionwas extracted by ethyl acetate (3×20 ml)
- customThe organic phase was evaporated in vacuo
Sources & evidence
- ORD record
- ord-f8ff005f7298447b89adeb23e8bd7e85
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778939B2
Reaction notes
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