Hydrochloric Acid → 4,5,6,7-Tetrafluorobenzothiophen-2-carboxylic acid

HRID 359551

Reaction equation

HRID 359551 reaction equation
F[C:2]1[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[C:12]([F:19])[C:3]=1[CH:4]=[C:5]1[S:9]C(=S)N[C:6]1=[O:11].[OH-:20].[Na+].Cl>O>[F:19][C:12]1[C:3]2[CH:4]=[C:5]([C:6]([OH:20])=[O:11])[S:9][C:2]=2[C:15]([F:16])=[C:14]([F:17])[C:13]=1[F:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 49072912,3,4,5,6-Pentafluorobenzylidene rhodanine

Product 1

HCID 109886834,5,6,7-Tetrafluorobenzothiophen-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

78 g of 2,3,4,5,6-pentafluorobenzylidene rhodanine were added in small portions to a stirred solution of 68 g of NaOH in 300 ml of water. The resultant clear red solution was heated to 90° C. for one hour, cooled in ice, acidified with concentrated HCl, and the cream coloured solid which was produced was filtered and washed. The crude product (59 g) was purified by sublimation to give 4,5,6,7-tetrafluorobenzothiophen-2-carboxylic acid having a melting point of 200° C.

Workup

  1. temperaturecooled in ice
  2. customwas produced
  3. filtrationwas filtered
  4. washwashed
  5. customThe crude product (59 g) was purified by sublimation

Sources & evidence

ORD record
ord-6cf3f054d9ff4d0bb059e798eeecbbd0
Source dataset
uspto-grants-1991_03
Patent number
US05001163

Linked notes

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