p-Toluenesulfonic acid → 6-Bromo-4-methyl-7-ethoxy-2,2-dimethyl-2H-chromene

HRID 2180466Notes

Reaction equation

HRID 2180466 reaction equation
C[Mg]Cl.[Br:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH2:16][CH3:17])[O:11][C:10]([CH3:19])([CH3:18])[CH2:9][C:8]2=O.[C:21]1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[Br:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH2:16][CH3:17])[O:11][C:10]([CH3:19])([CH3:18])[CH:9]=[C:8]2[CH3:21]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 224909226-Bromo-7-ethoxy-2,2-dimethyl-chroman-4-one2×HCID 178418332HCID 178418332, compound

Product 1

HCID 224910906-Bromo-4-methyl-7-ethoxy-2,2-dimethyl-2H-chromene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following General Procedure C, methylmagnesium chloride (3 M in THF, 1.38 mL, 4.14 mmol) was added to a solution of 6-bromo-7-ethoxy-2,2-dimethyl-chroman-4-one (Compound 5, 588 mg, 2.07 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-44ae1f6f6e6f4575a9ba409cc6f97e5b
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

Loading…