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

HRID 2180464Notes

Reaction equation

HRID 2180464 reaction equation
[C:1]([Mg]Cl)([CH3:4])([CH3:3])[CH3:2].[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[O:14][C:13]([CH3:21])([CH3:20])[CH2:12][C:11]2=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[O:14][C:13]([CH3:21])([CH3:20])[CH:12]=[C:11]2[C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 134522776-Bromo-7-methoxy-2,2-dimethyl-chroman-4-one2×HCID 178418310HCID 178418310, compound

Product 1

HCID 224909336-Bromo-4-tert-butyl-7-methoxy-2,2-dimethyl-2H-chromene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following General Procedure C, tert-butylmagnesium chloride (1.0 M in THF, 45.5 mL, 45.5 mmol) was added to a solution of 6-bromo-7-methoxy-2,2-dimethyl-chroman-4-one (Compound 4, 2.6 g, 9.1 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-8bcf1882e82c47b289c5933d7470dcf1
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

Loading…