Sulfuric Acid → Benzenepropanoic acid, beta-oxo-3-(trifluoromethyl)-

HRID 1062020Notes

Reaction equation

HRID 1062020 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].C[Si]([C:18]([Si](C)(C)C)([C:22]([O-:24])=[O:23])[C:19]([O-:21])=[O:20])(C)C.CCN([CH2:34][CH3:35])CC.[Li+].[Br-].OS(O)(=O)=O.[CH3:43]C#N>C(OC(C)=C)(=O)C>[O:7]=[C:6]([C:5]1[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:13])([F:12])[F:1])[CH:4]=1)[CH2:18][C:19]([OH:21])=[O:20].[CH3:43][C:34]1([CH3:35])[O:24][C:22](=[O:23])[CH:18]=[C:6]([C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:13])([F:12])[F:1])[CH:4]=2)[O:7]1

Participants

9

Reactant 6

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 8471TriethylamineHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 82050Lithium BromideHCID 222245802,2-Bis(trimethylsilyl)propanedioate

Product 2

HCID 17819988Benzenepropanoic acid, beta-oxo-3-(trifluoromethyl)-HCID 22224716HCID 22224716, compound

Reagents, catalysts & solvents 1

HCID 7916Isopropenyl acetateSolvent

Procedure

The 3-oxo-3-(3-trifluoromethyl-phenyl)-propionic acid was prepared from 3-trifluoromethylbenzoyl chloride (10 mL, 67.6 mmol) and bis(trimethylsilyl)malonate (18.2 mL, 71 mmol) with Et3N (20 mL, 142 mmol) and LiBr (6.46 g, 74.4 mmol) in CH3CN at 0° C. according to general procedure H (method c1). The crude material (7.0 g of the obtained 15.4 g) was transformed into the title compound by stirring in isopropenyl acetate and conc. H2SO4 according to general procedure J (method a). Obtained as a light yellow solid (5.3 g).

Sources & evidence

ORD record
ord-bbf94bdabe2144f2be0b686101070abb
Source dataset
uspto-grants-2005_11
Patent number
US06960578B2

Reaction notes

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