p-Toluenesulfonic acid → 6-bromo-4-isopropyl-7-methoxy-2,2-dimethyl-2H-chromene

HRID 2180463Notes

Reaction equation

HRID 2180463 reaction equation
[CH:1]([Mg]Cl)([CH3:3])[CH3:2].[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[O:13][C:12]([CH3:20])([CH3:19])[CH2:11][C:10]2=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[O:13][C:12]([CH3:20])([CH3:19])[CH:11]=[C:10]2[CH:1]([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 134522776-Bromo-7-methoxy-2,2-dimethyl-chroman-4-one2×HCID 178418918HCID 178418918, compound

Product 1

HCID 224908876-bromo-4-isopropyl-7-methoxy-2,2-dimethyl-2H-chromene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following General Procedure C, isopropylmagnesium chloride (2.0 M in THF, 6.1 mL, 21.3 mmol) was added to a solution of 6-bromo-7-methoxy-2,2-dimethyl-chroman-4-one (Compound 4, 700 mg, 2.46 mmol) in THF. The crude alcohol was treated with p-toluenesulfonic acid to afford the title compound as a colorless oil.

Sources & evidence

ORD record
ord-10e8b24d37954188bed10a94a4f35677
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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