Hydrochloric Acid → 8-Fluoro-1,2,3,4-tetrahydrodibenzo[b,d]thiophene-2-carboxylic acid

HRID 1593617Notes

Reaction equation

HRID 1593617 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]3[CH2:10][CH2:11][CH:12]([C:14]([O:16]CC)=[O:15])[CH2:13][C:7]=3[C:6]=2[CH:19]=1.[OH-].[K+].Cl.O>CCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]3[CH2:10][CH2:11][CH:12]([C:14]([OH:16])=[O:15])[CH2:13][C:7]=3[C:6]=2[CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 69235740Ethyl 8-fluoro-1,2,3,4-tetrahydrodibenzo[b,d]thiophene-2-carboxylate

Product 1

HCID 692352028-Fluoro-1,2,3,4-tetrahydrodibenzo[b,d]thiophene-2-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of ethyl 8-fluoro-1,2,3,4-tetrahydrodibenzo[b,d]thiophene-2-carboxylate (2.5 g, 9 mmol) in EtOH (60 mL) was added KOH (0.81 g, 15 mmol). The reaction was stirred at 40° C. overnight. After cooling in an ice-water bath, the mixture was acidified to pH 2-3 with 1 N HCl. Water was added and the resulting white solid precipitate was collected and dried to afford 2.15 g (96%) of the title compound: mp 245° C. (dec.), MS (−) 249 (M−H)−.

Workup

  1. temperatureAfter cooling in an ice-water bath
  2. customthe resulting white solid precipitate was collected
  3. customdried

Sources & evidence

ORD record
ord-7cc9e1ec658c4b528687701fb5afb218
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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