Boron tribromide → 7-Amino-8-hydroxy-3-iodo-2-phenyl-chromen-4-one
Reaction equation
[NH2:1][C:2]1[C:11]([O:12]C)=[C:10]2[C:5]([C:6](=[O:21])[C:7]([I:20])=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:9]2)=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:1][C:2]1[C:11]([OH:12])=[C:10]2[C:5]([C:6](=[O:21])[C:7]([I:20])=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:9]2)=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 7-amino-3-iodo-8-methoxy-2-phenyl-chromen-4-one (494 mg, 1.26 mmol) in DCM (25 mL) under a nitrogen atmosphere at −78° C. was added a solution of BBr3 (1 M in DCM, 8 mL, 8 mmol) dropwise over 15 mins. The mixture was stirred at −78° C. for 1 hour before allowing to warm to RT and stirred for a further 18 hours. The reaction mixture was quenched with the slow addition of saturated aqueous NaHCO3. DCM was added and the resulting biphasic mixture was separated. The aqueous layer was extracted with DCM (2×50 mL) and the combined organic phase was washed with brine, dried (NaSO4), filtered, and the solvent removed to give the title compound as a brown solid (405 mg, 85%). LCMS (Method G): RT=3.04 min, [M+H]+=380.
Workup
- temperatureto warm to RT
- stirringstirred for a further 18 hours
- customThe reaction mixture was quenched with the slow addition of saturated aqueous NaHCO3
- additionDCM was added
- customthe resulting biphasic mixture was separated
- extractionThe aqueous layer was extracted with DCM (2×50 mL)
- washthe combined organic phase was washed with brine
- dry with materialdried (NaSO4)
- filtrationfiltered
- customthe solvent removed
Sources & evidence
- ORD record
- ord-7193569dd6974b5caff581f3a341131f
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546376B2
Reaction notes
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