Acetone → HCID 11657313, compound
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([OH:17])=[CH:16][C:11]=3[S:10][N:9]=2)=[CH:4][CH:3]=1.[F:18][C:19]([F:34])([F:33])[C:20]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)([OH:25])[C:21]([F:24])([F:23])[F:22].C([O-])([O-])=O.[Cs+].[Cs+].[I-].[K+].[CH3:43][C:44]([CH3:46])=O>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([O:17][CH2:43][CH2:44][CH2:46][O:32][C:29]4[CH:30]=[CH:31][C:26]([C:20]([OH:25])([C:21]([F:23])([F:22])[F:24])[C:19]([F:33])([F:34])[F:18])=[CH:27][CH:28]=4)=[CH:16][C:11]=3[S:10][N:9]=2)=[CH:6][CH:7]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
100 mg (0.23 mmol) of 3-(4-bromo-phenyl)-benzo[d]isothiazol-6-ol (CAS 423159-55-1, prepared as described in WO 2002036584) in 2 ml of acetone were treated with 67 mg (0.22 mmol) of 4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenol (example 6), 76 mg (0.2 mmol) of Cs2CO3 and 8 mg (0.05 mmol) of potassium iodide. The reaction mixture was stirred at ambient temperature for 2.5 d, at 45° C. for 4 h, and then was diluted with dichloromethane. The organic phase was washed with water and brine, dried (Na2SO4) and evaporated. The crude product was purified by column chromatography on silica gel to yield 40 mg (28%) 2-(4-{3-[3-(4-bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-propoxy}-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol as a colorless solid, MS: 604 (M−H, 1Br)−.
Workup
- washThe organic phase was washed with water and brine
- dry with materialdried (Na2SO4)
- customevaporated
- customThe crude product was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-618809ab59474615921f0a9ba324836e
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473705B2
Reaction notes
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