Nitrogen → 2-Methyl-4-(1-methylcyclopropyl)benzoyl chloride
Reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([C:11]2([CH3:14])[CH2:13][CH2:12]2)[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].P(Cl)(Cl)(Cl)(Cl)[Cl:16].N#N>>[CH3:1][C:2]1[CH:10]=[C:9]([C:11]2([CH3:14])[CH2:13][CH2:12]2)[CH:8]=[CH:7][C:3]=1[C:4]([Cl:16])=[O:5]Participants
4
Procedure
2-Methyl-4-(1-methyl-cyclopropyl)-benzoic acid (2.139 g, 11.243 mmol) and phosphoruspentachloride (2.575 g, 12.37 mmol) were charged into a 50 ml flask under stirring. These both solids dissolved at 100° C. The reaction mixture was stirred 2 hours at 120° C. with an reflux condenser in a N2 atmosphere. After that the resulting phosphorus oxylchloride was distilled off at 140° C. from the reaction mixture. The whole reaction mixture was cooled to room temperature and the reaction mixture still remained as a solution. The desired product was distilled by Kugelrohr distillation (150° C./4 mbar) to give 2-Methyl-4-(1-methyl-cyclopropyl)-benzoyl chloride (1.92 g, 9.2 mmol)
Workup
- dissolutionThese both solids dissolved at 100° C
- distillationAfter that the resulting phosphorus oxylchloride was distilled off at 140° C. from the reaction mixture
- customThe whole reaction mixture
- distillationThe desired product was distilled by Kugelrohr distillation (150° C./4 mbar)
Sources & evidence
- ORD record
- ord-386005508ce64928b3352b53594387be
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536166B2
Reaction notes
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