HCID 22313952, compound → HCID 135847955, compound

HRID 966161Notes

Reaction equation

HRID 966161 reaction equation
C[O:2][C:3]1[CH:21]=[CH:20][C:6]2[C:7]([C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=3)=[N:8][S:9][C:5]=2[CH:4]=1>C(O)(=O)C.Br>[F:19][C:16]([F:17])([F:18])[C:13]1[CH:12]=[CH:11][C:10]([C:7]2[C:6]3[CH:20]=[CH:21][C:3]([OH:2])=[CH:4][C:5]=3[S:9][N:8]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 22313952HCID 22313952, compound

Product 1

HCID 135847955HCID 135847955, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Conditions

Temperature
3 °C

Procedure

A solution of 20 g (64.66 mmol) of 6-Methoxy-3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazole in 150 ml of acetic acid and 75 ml 62% aqueous HBr solution was heated to reflux for 70 h, subsequently cooled and taken up in ice water and extracted with tert-butylmethyleter (3×). The organic phases were washed with saturated sodium hydrogen carbonate solution (3×) and dried (Na2SO4). The residue was suspended in 350 ml boiling CH2Cl2, cooled to 3° C. and filtered to yield 15.8 g (83%) of 3-(4-Trifluoromethyl-phenyl)-benzo[d]isothiazol-6-ol, MS: 295 (M).

Workup

  1. temperatureto reflux for 70 h
  2. temperaturesubsequently cooled
  3. extractionextracted with tert-butylmethyleter (3×)
  4. washThe organic phases were washed with saturated sodium hydrogen carbonate solution (3×)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-04794b492149453fa88a3780c9e9ddac
Source dataset
uspto-grants-2005_10
Patent number
US06951879B2

Reaction notes

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