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Trifluoroacetic acid → 2,5-Dichloro-3-methoxybenzenethiol

HRID 591427
Notes
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Reaction equation

HRID 591427 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 897678422,5-Dichloro-1-methoxy-3-((4-methoxybenzyl)sulfanyl)benzene

Product 1

HCID 1186560892,5-Dichloro-3-methoxybenzenethiolYield 67.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc
  3. extractionThe organic layer was extracted with 1N NaOH
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-e03f806d7cc8423dbeaf99ad107404bf
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09238639B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes