Trifluoroacetic acid → 2,5-Dichloro-3-methoxybenzenethiol
Reaction equation
[Cl:1][C:2]1[C:7]([S:8]CC2C=CC(OC)=CC=2)=[CH:6][C:5]([Cl:18])=[CH:4][C:3]=1[O:19][CH3:20].C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>O>[Cl:1][C:2]1[C:3]([O:19][CH3:20])=[CH:4][C:5]([Cl:18])=[CH:6][C:7]=1[SH:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
The mixture of 2,5-dichloro-1-methoxy-3-((4-methoxybenzyl)sulfanyl)benzene (5.56 g) and anisole (9.18 mL) was added TFA (22.13 mL) at room temperature. The mixture was stirred at 80° C. for 20 min. After cooling, the mixture was diluted with water and extracted with EtOAc. The organic layer was extracted with 1N NaOH. The aqueous layer was acidified with 1N HCl, and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (2.38 g).
Workup
- temperatureAfter cooling
- extractionextracted with EtOAc
- extractionThe organic layer was extracted with 1N NaOH
- extractionextracted with EtOAc
- washThe organic layer was washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel column chromatography (EtOAc/hexane)
Sources & evidence
- ORD record
- ord-e03f806d7cc8423dbeaf99ad107404bf
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238639B2
Reaction notes
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