Phosphorus tribromide → 2-(Bromomethyl)-7-methoxy-1-benzofuran
Reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][C:9]([CH:12]=O)=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+].P(Br)(Br)[Br:17]>CCO>[Br:17][CH2:12][C:9]1[O:10][C:11]2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=2[CH:8]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Compound 29 (450 mg, 2.56 mmol) was dissolved in EtOH (10 mL). NaBH4 (104 mg, 2.81 mmol) was added portionwise at 0° C., with vigorous stirring. The suspension was stirred at 0° C. for 15 min and then at room temperature for 1.5 h. Solvent was evaporated off in-vacuo. The resulting crude alcohol residue was dissolved in toluene (5 mL) and the solution was cooled to 0° C. PBr3 (240 μL, 2.56 mmol) was added dropwise over 10 min.
Workup
- waitat room temperature for 1.5 h
- customSolvent was evaporated off in-vacuo
- dissolutionThe resulting crude alcohol residue was dissolved in toluene (5 mL)
- temperaturethe solution was cooled to 0° C
Sources & evidence
- ORD record
- ord-cf1de449634244f3ac8edcf30e68cc10
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08283340B2
Reaction notes
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