p-Toluenesulfonic acid → 6-Bromo-4-ethyl-7-methoxy-2,2-dimethyl-2H-chromene

HRID 2180462Notes

Reaction equation

HRID 2180462 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[Br:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[O:12][C:11]([CH3:19])([CH3:18])[CH2:10][C:9]2=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[Br:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[O:12][C:11]([CH3:19])([CH3:18])[CH:10]=[C:9]2[CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 134522776-Bromo-7-methoxy-2,2-dimethyl-chroman-4-one2×HCID 178418443HCID 178418443, compound

Product 1

HCID 224908636-Bromo-4-ethyl-7-methoxy-2,2-dimethyl-2H-chromene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following General Procedure C, ethylmagnesium bromide (2.0 M in THF, 4.7 mL, 14.08 mmol) was added to a solution of 6-bromo-7-methoxy-2,2-dimethyl-chroman-4-one (Compound 4, 800 mg, 2.81 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-7ee37f9dad74489d90df1bb2c7d683d3
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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