Isopropyl iodide → 6-Bromo-7-isopropoxy-2,2-dimethyl-chroman-4-one

HRID 2180456Notes

Reaction equation

HRID 2180456 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][C:7]([CH3:14])([CH3:13])[CH2:6][C:5]2=[O:15].C(=O)([O-])[O-].[K+].[K+].I[CH:23]([CH3:25])[CH3:24]>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH:23]([CH3:25])[CH3:24])[O:8][C:7]([CH3:13])([CH3:14])[CH2:6][C:5]2=[O:15]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 224908286-Bromo-7-hydroxy-2,2-dimethyl-chroman-4-one2×

Product 1

HCID 224909096-Bromo-7-isopropoxy-2,2-dimethyl-chroman-4-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

As described in General Procedure A, 6-bromo-7-hydroxy-2,2-dimethyl-chroman-4-one, (Compound 3, 1.0 g, 3.8 mmol) in acetone (50 mL) was treated with anhydrous potassium carbonate (2.1 g, 14.9 mmol) and 2-iodopropane (0.7 mL, 7.5 mmol) to give the title compound as a white solid after purification by flash chromatography (silica gel, 10% ethyl acetate in hexanes).

Sources & evidence

ORD record
ord-81f7acc181a84164a807bfd5797d041f
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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