2-Mercaptobenzoic Acid → 1-Fluoro-4-hydroxy-9H-thioxanthen-9-one

HRID 1825777Notes

Reaction equation

HRID 1825777 reaction equation
[C:1](O)(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[F:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1>OS(O)(=O)=O>[F:11][C:12]1[C:17]2[C:1](=[O:9])[C:2]3[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=3)[S:4][C:16]=2[C:15]([OH:18])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 54432-Mercaptobenzoic AcidHCID 97324-Fluorophenol

Product 1

HCID 136150131-Fluoro-4-hydroxy-9H-thioxanthen-9-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Thiosalicylic acid (46.26 g, 0.3 mol) and 4-fluorophenol (56.05 g, 0.5 mol) were dissolved in conc. H2SO4 (750 ml) and the mixture was stirred under nitrogen for 24 hours. The reaction mixture was then poured onto ice (1.5 L) and the yellow precipitate was filtered and washed with water (300 ml). The precipitate was dried at 50° C. for 24 hours and was used without further purification (31.4 g, 42.5%). m/z (LC-MS, ESP): 247 (M++1).

Workup

  1. additionThe reaction mixture was then poured onto ice (1.5 L)
  2. filtrationthe yellow precipitate was filtered
  3. washwashed with water (300 ml)
  4. customThe precipitate was dried at 50° C. for 24 hours
  5. customwas used without further purification (31.4 g, 42.5%)

Sources & evidence

ORD record
ord-ca64ecd7d1f44a04ad3ef6d358093146
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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