Water → 7-Fluoro-benzo[d]isothiazole-6-carboxylic acid

HRID 79014Notes

Reaction equation

HRID 79014 reaction equation
C([O:5][C:6]([C:8]1[CH:16]=[CH:15][C:11]2[CH:12]=[N:13][S:14][C:10]=2[C:9]=1[F:17])=[O:7])(C)(C)C.O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:17][C:9]1[C:10]2[S:14][N:13]=[CH:12][C:11]=2[CH:15]=[CH:16][C:8]=1[C:6]([OH:7])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 575231267-Fluoro-benzo[d]isothiazole-6-carboxylic acid tert-butyl ester

Product 1

HCID 583743747-Fluoro-benzo[d]isothiazole-6-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-fluoro-benzo[d]isothiazole-6-carboxylic acid tert-butyl ester (1.0 g, 4.0 mmol) in DCM (10 mL) was added water (0.2 mL) and TFA (10 mL). There reaction mixture was stirred at room temperature for 1 hour and concentrated in vacuo. The residue was azeotroped with toluene to give the title compound as a yellow solid (788 mg, 100%). LCMS (method B): RT=2.86 min, [M−H]−=196.

Workup

  1. customThere reaction mixture
  2. concentrationconcentrated in vacuo
  3. customThe residue was azeotroped with toluene

Sources & evidence

ORD record
ord-8094a7ccb8ff433cae34d8ec42055cda
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

Loading…