Hydrochloric Acid → 2-(Benzyloxy)-5-bromobenzoic acid
Reaction equation
[Li+].[OH-].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:8]([CH:19]=1)[C:9]([O:11]CC1C=CC=CC=1)=[O:10].C1COCC1.Cl>C(OCC)(=O)C.O>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:8]([CH:19]=1)[C:9]([OH:11])=[O:10]Participants
7
Conditions
- Temperature
- 71 °C
Procedure
Solid LiOH (1.01 g, 42.1 mmol) was added in a single charge to a stirred solution of phenylmethyl 5-bromo-2-[(phenylmethyl)oxy]benzoate (may be prepared as described in Description 4, method B; 3 g, 7.55 mmol) in a 3:1 mixture of THF and water (40 ml) at 20° C. The reaction mixture was stirred at 71° C. for 16 h. After cooling to room temperature, it was diluted with ethyl acetate (200 ml). 10% aqueous HCl was added to the mixture to adjust the pH to 2. The organic phase was isolated, washed with brine, dried over Na2SO4, and concentrated to give a white solid. The crude product was purified by silica gel chromatography eluting with hexane:ethyl acetate (3:1) to yield the title compound as white solid. 2.1 g.
Workup
- temperatureAfter cooling to room temperature
- customThe organic phase was isolated
- washwashed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customto give a white solid
- customThe crude product was purified by silica gel chromatography
- washeluting with hexane:ethyl acetate (3:1)
Sources & evidence
- ORD record
- ord-81713152c83c420195564acdb4a5c653
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778939B2
Reaction notes
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