Ammonium Chloride → 5-Bromo-2,3-dihydro-1-benzofuran
Reaction equation
[Br:1][C:2]1[CH:10]=[C:9](Br)[C:5]2[O:6][CH2:7][CH2:8][C:4]=2[CH:3]=1.C([Li])CCC.[Cl-].[NH4+]>C(OCC)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]2[O:6][CH2:7][CH2:8][C:4]=2[CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
5,7-Dibromo-2,3-dihydrobenzo[b]furan (see WO 02/070020) (3.0 g) in diethyl ether was cooled to −78° C. under argon atmosphere, and thereto was added dropwise n-butyl lithium (2.44 M hexane solution, 5.09 ml). The mixture was stirred at the same temperature for 30 minutes, and poured into a saturated aqueous ammonium chloride solution. The mixture was extracted with diethyl ether, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give 5-bromo-2,3-dihydrobenzo[b]furan (2.0 g) as pale yellow crystals, which was used in the subsequent step without further purification.
Workup
- extractionThe mixture was extracted with diethyl ether
- dry with materialdried over magnesium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-f8cebef5cad44beab38126a228da36c9
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785403B2
Reaction notes
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