Lithium Hydroxide → 5-Bromo-2-[(4-chlorophenyl)methoxy]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][C:26]([Cl:29])=[CH:25][CH:24]=2)=[C:8]([CH:20]=1)[C:9]([O:11]CC1C=CC(Cl)=CC=1)=[O:10]>O.C1COCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=2)=[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 (164 mg, 6.86 mmol) in water (20.00 mL) was added dropwise to a stirred solution of (4-chlorophenyl)methyl 5-bromo-2-{[(4-chlorophenyl)methyl]oxy}benzoate (may be prepared as described in Description 15; 320 mg, 0.69 mmol) in THF (20 ml) over 5 min. The reaction mixture was then stirred at 20° C. for 16 h. The organic phase was evaporated and the residual aqueous phase (20 ml) was extracted with ethyl acetate (20 ml). The aqueous phase (20 ml) was adjusted to pH 2 with 2M hydrochloric acid (1 ml) and was extracted with ethyl acetate (3×20 ml). The organic phase was evaporated in vacuo to give the title compound as a light yellow solid. 180 mg.
Workup
- customThe organic phase was evaporated
- extractionthe residual aqueous phase (20 ml) was extracted with ethyl acetate (20 ml)
- extractionwas extracted with ethyl acetate (3×20 ml)
- customThe organic phase was evaporated in vacuo
Sources & evidence
- ORD record
- ord-258d84ea2d3a4f8894da23b0a0e7cedd
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778939B2
Reaction notes
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