Boron tribromide → HCID 57678422, compound
Reaction equation
[I:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([I:10])=[CH:4][C:3]=1[O:11]C.B(Br)(Br)Br>ClCCl>[I:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([I:10])=[CH:4][C:3]=1[OH:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1,4-Diiodo-2,5-dimethoxy-benzene (3.65 g, 9.36 mmol) was added to 100 mL of dichloromethane and stirred under nitrogen at ice bath temperature. Boron tribromide (10.3 mL, 10.3 mmol) was added dropwise, and the reaction mixture was stirred at ice bath temperature for 20 hours. The reaction was quenched by dropwise addition of methanol, and the reaction mixture was poured into water and extracted into dichloromethane. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give 2.86 g of 2,5-Diiodo-4-methoxy-phenol, MS (M+H)=377.
Workup
- stirringthe reaction mixture was stirred at ice bath temperature for 20 hours
- customThe reaction was quenched by dropwise addition of methanol
- additionthe reaction mixture was poured into water
- extractionextracted into dichloromethane
- washThe combined organic layers were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-ae80a5a89a094180acc3084843b49ba3
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07531547B2
Reaction notes
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