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

HRID 1825788Notes

Reaction equation

HRID 1825788 reaction equation
[CH:1]1[CH:6]=[C:5]([C:7](O)=[O:8])[C:4]([SH:10])=[CH:3][CH:2]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1>S(=O)(=O)(O)O>[F:11][C:12]1[C:17]2[C:7](=[O:8])[C:5]3[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=3)[S:10][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-oneYield 70.8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 2-thiosalicylic acid (39.32 g, 255 mmol) in concentrated sulfuric acid (700 ml) was added 4-fluorophenol (32.0 g, 280 mmol). The red solution was then stirred at room temperature for 18 hours. Upon completion, the mixture was poured directly onto 4 liters of crushed ice and the resulting red solid was filtered off, and then suspended in water (1 L)and treated with ammonia solution until pH 6 attained whereupon the precipitate was re-filtered to give the title compound as an orange solid (44.48 g, 70.8%) m/z (LC-MS, ESP): 247 [M+H]+, R/T=3.99 mins

Workup

  1. filtrationthe resulting red solid was filtered off
  2. additiontreated with ammonia solution until pH 6
  3. filtrationwas re-filtered

Sources & evidence

ORD record
ord-c5f32671de1c4b39a19e246864430492
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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