Boron tribromide → 1,3-Benzenediol, propyl-
Reaction equation
C[O:2][C:3]1[C:8]([CH2:9][CH2:10][CH3:11])=[C:7]([O:12]C)[CH:6]=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[C:8]([CH2:9][CH2:10][CH3:11])=[C:7]([OH:12])[CH:6]=[CH:5][CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
2,4,-Dimethoxy-3-propylbenzene (7.2 g, 39.94 mmol) was dissolved in 50 ml methylene chloride and the solution was cooled to -70° C. then 87.0 ml of 1M boron tribromide in methylene chloride was added over a period of 1 hour. The reaction mixture was stirred at -70° C. for 1 hour, then at room temperature for 2 hours. The reaction mixture was poured into 250 ml of ice water very slowly. This mixture was extracted 3 times with 100 ml methylene chloride. The extracts were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under vacuum to give the product as a white solid (4.9 g, 81.7%).
Workup
- waitat room temperature for 2 hours
- extractionThis mixture was extracted 3 times with 100 ml methylene chloride
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customthe solvent was removed under vacuum
Sources & evidence
- ORD record
- ord-cad34db0410d48758629d209df634ebd
- Source dataset
- uspto-grants-1994_05
- Patent number
- US05310951
Reaction notes
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