Boron tribromide → 4-Bromo-6-hydroxy-2,3-dihydro-1H-isoindol-1-one
Reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([O:11]C)[CH:8]=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:13].B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A −78° C. suspension of Example 104A (100 mg, 0.41 mmol) in dichloromethane (13 mL) was treated dropwise with 1M BBr3 in dichloromethane (1.2 mL, 1.2 mmol), stirred at −78° C. for 1 hour, and stirred at room temperature for 2 hours. The mixture was treated with additional 1M BBr3 in dichloromethnae (0.8 mL), heated to reflux overnight, then cooled to room temperature, and partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4), filtered, and concentrated to give 91 mg (97%) of the desired product. MS (ESI(−)) m/226, 228 (M−H)−.
Workup
- stirringstirred at room temperature for 2 hours
- temperatureheated
- temperatureto reflux overnight
- temperaturecooled to room temperature
- custompartitioned between water and ethyl acetate
- dry with materialThe organic phase was dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e133d9d73ecd47e898303bac7b3c48b2
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07129260B2
Reaction notes
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