Dimethyl Sulfide → 1-[(E)-3-Chloro-1-methyl-1-propenyl]-3-nitrobenzene
Reaction equation
[Cl:1]N1C(=O)CCC1=O.CSC.[N+:12]([C:15]1[CH:16]=[C:17](/[C:21](/[CH3:25])=[CH:22]/[CH2:23]O)[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13]>ClCCl>[Cl:1][CH2:23]/[CH:22]=[C:21](/[C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=1)\[CH3:25]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of N-chlorosuccinimide (52.3 g, 0.39 mol) in dichloromethane (800 ml) at 0° C. was added dropwise over 1 h dimethylsulfide (27.9 ml, 0.38 mol). To the mixture was added dropwise over 30 min at 0° C. a solution of (E)-3-(3-nitrophenyl)-2-buten-1-ol (Preparation 2, 72 g, 0.373 mol) in dichloromethane (200 ml). The mixture was warmed to room temperature over 1 h, then poured onto brine (500 ml). The layers were separated, and the aqueous layer extracted with ether (500 ml). The organic extracts were combined, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica column chromatography, eluting with 10:1 hexane/ethyl acetate, then kas a gradient up to 4:1 hexane/ethyl acetate. Appropriate fractions were combined and concentrated in vacuo to give the title compound as a very pale yellow solid (69 g, 88%).
Workup
- additionpoured onto brine (500 ml)
- customThe layers were separated
- extractionthe aqueous layer extracted with ether (500 ml)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by silica column chromatography
- washeluting with 10:1 hexane/ethyl acetate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-543c368212f74ee7ba333bc6bddf7466
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06313312B1
Reaction notes
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