Thionyl Chloride → 1-Indanone, 4-bromo-
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([OH:12])=O.S(Cl)(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH2:8][CH2:9][C:10]2=[O:12]Participants
Conditions
- Temperature
- 0 °C
Procedure
128.2 g (0.559 mol) of 3-(2-Bromo-phenyl)-propionic acid are placed in a 2-neck round bottom flask with gas outlet and stirrer. 133.2 g (1.12 mol) of thionyl chloride are added and the mixture is heated under reflux for 2 h with stirring in an argon atmosphere and excess thionyl chloride is removed in a vacuum. The resulting yellow oil is dissolved in 700 ml of methylene chloride, cooled to 0° C. and 82.0 g (0.615 mol) anhydrous aluminium chloride are added in small portions. The reaction mixture is stirred at 0° C. for 2 h and then hydrolyzed by carefully pouring it on crushed ice. The organic layer is separated. The aqueous layer is acidified with concentrated hydrochloric acid and extracted twice with methylene chloride. The combined organic layers are washed once with 2 M HCl, once with water, dried over anhydrous magnesium sulphate and the solvent is removed under reduced pressure (110.0 g, 87%).
Workup
- temperaturethe mixture is heated
- temperatureunder reflux for 2 h
- customis removed in a vacuum
- dissolutionThe resulting yellow oil is dissolved in 700 ml of methylene chloride
- additionby carefully pouring it
- customon crushed ice
- customThe organic layer is separated
- extractionextracted twice with methylene chloride
- washThe combined organic layers are washed once with 2 M HCl, once with water
- dry with materialdried over anhydrous magnesium sulphate
- customthe solvent is removed under reduced pressure (110.0 g, 87%)
Sources & evidence
- ORD record
- ord-36138ee4ee2d4184ab5ec6a5e57a2744
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415492B2
Reaction notes
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