(Diethylamino)sulfur trifluoride → HCID 58409089, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9](O)[CH:10]([N+:12]([O-:14])=[O:13])[CH3:11].CCN(S(F)(F)[F:22])CC>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([F:22])[CH:10]([N+:12]([O-:14])=[O:13])[CH3:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
To a stirred mixture of erythro 1-(2,4-dichlorophenyl)-2-nitro-propan-1-ol (2.5 g, 10.0 mmol) in dry dichloromethane (20 ml) under nitrogen atmosphere DAST (1.3 ml, 10.0 mmol) in dichloromethane (5 ml) was added dropwise under cooling to 5° C. The solution was stirred at ambient temperature for 1 hour. Dichloromethane (80 ml) was added and the organic layer was washed sequentially with saturated NaHCO3 (50 ml), 1M HCl (30 ml) and sole (30 ml). The organic layer was dried over NaSO4, filtered, and concentrated. 2.5 g of 2,4-dichloro-1-(1-fluoro-2-nitro-propyl)-benzene was obtained in the form of a brown oil.
Workup
- additionwas added dropwise
- washthe organic layer was washed sequentially with saturated NaHCO3 (50 ml), 1M HCl (30 ml) and sole (30 ml)
- dry with materialThe organic layer was dried over NaSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-048518da9ad340e3bb03955f4768de6b
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258169B2
Reaction notes
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