Potassium Hydroxide → (2-Chloro-6-nitrophenyl)(3-chloropropyl)sulfane
Reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Cl:12][CH2:13][CH2:14][CH2:15][SH:16].[OH-].[K+]>C1COCC1>[Cl:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([N+:9]([O-:11])=[O:10])[C:2]=1[S:16][CH2:15][CH2:14][CH2:13][Cl:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
To a dry THF (Aldrich anhydrous grade, 70 mL) solution of 2,3-dichloronitrobenzene (9.61 g, 50.1 mmol) and 3-chloropropanethiol (5.0 g, 45.5 mmol) was added in one portion at 23° C. KOH pellets. The resulting mixture was vigorously stirred at 23° C. for 3.5 h. The reaction mixture was filtered through a Celite plug to remove remaining KOH. The plug was washed with THF (2×50 mL). The filtrate was concentrated in vacuo to give crude 1-chloro-2-[(3-chloropropyl)sulfanyl]-3-nitrobenzene (12 g, ˜100%).
Workup
- filtrationThe reaction mixture was filtered through a Celite plug
- customto remove
- washThe plug was washed with THF (2×50 mL)
- concentrationThe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-a9c15ca7bb9e4f46bb5ac21caee1abe9
- Source dataset
- uspto-grants-2007_06
- Patent number
- USRE039679E1
Reaction notes
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