Potassium Hydroxide → 4-Bromo-3-methylbenzene-1-thiol
Reaction equation
CN(C)C(=O)[S:4][C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([CH3:12])[CH:6]=1.[OH-].[K+]>CO>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([SH:4])=[CH:6][C:7]=1[CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of S-4-bromo-3-methylphenyl dimethylcarbamothioate (4.56 g, 16.6 mmol) and potassium hydroxide (3.27 g, 58.2 mmol) in MeOH was heated at 90° C. for 1 hour. The mixture was cooled to RT and concentrated. The residue was redissolved in DCM and aqueous sodium bicarbonate (sat.) and the layers were separated. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography (100% hexanes) to afford 2.84 g of 4-bromo-3-methylbenzenethiol as a pale yellow oil.
Workup
- temperatureThe mixture was cooled to RT
- concentrationconcentrated
- dissolutionThe residue was redissolved in DCM
- customaqueous sodium bicarbonate (sat.) and the layers were separated
- dry with materialThe organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude material was purified by silica gel chromatography (100% hexanes)
Sources & evidence
- ORD record
- ord-6add02a9154c413ab9c2978e3d096b19
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101612B2
Reaction notes
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