Sulfuric Acid → (2-Bromo-4,6-dichlorophenyl)methanol
Reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([Cl:12])[C:3]=1[C:4](O)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O.C(OCC)(=O)C>O1CCCC1.O>[Br:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([Cl:12])[C:3]=1[CH2:4][OH:5]Participants
7
Procedure
2.5 g of the acid 35.5 were dissolved in 25 ml of dry tetrahydrofuran and admixed dropwise at 0° C. with 9.26 ml of a 1 molar solution of lithium aluminum hydride in tetrahydrofuran with stirring. The reaction mixture was stirred at 0° C. for another 30 min and at room temperature for 2 h. For workup, the mixture was adjusted to pH 2 with 2.5 N sulfuric acid with cooling and admixed with ethyl acetate and water. The organic phase was removed, dried over magnesium sulfate and concentrated under reduced pressure. (2-Bromo-4,6-dichlorophenyl)methanol 35.4 was obtained and was used in the next stage without further purification.
Workup
- stirringThe reaction mixture was stirred at 0° C. for another 30 min and at room temperature for 2 h
- customThe organic phase was removed
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-6312fab6d51142d5b9f0580ba7fbba87
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07759366B2
Reaction notes
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