Trisodium Phosphate → 4-Fluoro-1-(trifluoromethyl)-2-({[4-(trifluoromethyl)phenyl]sulfonyl}methyl)benzene
Reaction equation
S([O-])([O-])=O.[Na+].[Na+].P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].[F:15][C:16]([F:28])([F:27])[C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.[F:29][C:30]([F:41])([F:40])[C:31]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:32]=1[CH2:33]Br>C(O)C.O.O1CCOCC1>[F:39][C:36]1[CH:37]=[CH:38][C:31]([C:30]([F:29])([F:40])[F:41])=[C:32]([CH2:33][S:23]([C:20]2[CH:21]=[CH:22][C:17]([C:16]([F:28])([F:27])[F:15])=[CH:18][CH:19]=2)(=[O:25])=[O:24])[CH:35]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
Sodium sulfite (102 g, 809 mmol) was added to sodium phosphate, dibasic (58 g, 409 mmol) and water (550 ml). 4-(trifluoromethyl)benzenesulfonyl chloride (100 g, 409 mmol) and dioxane (65 ml) were then added to the reaction mixture. The reaction was heated to reflux. After 75 min, the reaction was cooled slightly and a solution of 2-trifluoromethyl-5-fluoro-benzyl bromide (75 g, 292 mmol) in ethanol (95 ml) were added and the mixture was refluxed for 1 hr. The reaction was diluted with water (400 ml) and cooled to 0° C. for 1 hr. The reaction mixture was filtered and the solid was washed with water (2×400 ml) and then with heptane (200 ml). The residue was dried under vacuum to a constant weight and carried to the next step without further purification.
Workup
- temperatureThe reaction was heated to reflux
- temperaturethe reaction was cooled slightly
- temperaturethe mixture was refluxed for 1 hr
- filtrationThe reaction mixture was filtered
- washthe solid was washed with water (2×400 ml)
- customThe residue was dried under vacuum to a constant weight
- customcarried to the next step without further purification
Sources & evidence
- ORD record
- ord-34b56cd264c3448082cbb593b7fc1165
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609897B2
Reaction notes
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