N-methyl-2-pyrrolidone → 6,6'-Dimethyl-2,2',3',4'-tetramethoxy-5-trifluoromethyl-benzophenone

HRID 611719Notes

Reaction equation

HRID 611719 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:24][CH3:25])=[C:6]([C:22]=1[CH3:23])[C:7]([C:9]1[C:14]([CH3:15])=[CH:13][C:12]([O:16][CH3:17])=[C:11]([O:18][CH3:19])[C:10]=1[O:20][CH3:21])=[O:8].[F:26][C:27]([F:32])([F:31])C([O-])=O.[Na+].CN1CCCC1=O>CCOCC.O.[Cu]I>[CH3:23][C:22]1[C:6]([C:7]([C:9]2[C:14]([CH3:15])=[CH:13][C:12]([O:16][CH3:17])=[C:11]([O:18][CH3:19])[C:10]=2[O:20][CH3:21])=[O:8])=[C:5]([O:24][CH3:25])[CH:4]=[CH:3][C:2]=1[C:27]([F:32])([F:31])[F:26]

Participants

7

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 517019Sodium TrifluoroacetateHCID 6451057Metrafenone

Product 1

HCID 226713936,6'-Dimethyl-2,2',3',4'-tetramethoxy-5-trifluoromethyl-benzophenone

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 63C (6.15 g, 0.015 mol), sodium trifluoroacetate (9.52 g, 0.07 mol), copper-(I)iodide (13.37 g, 0.07 mol) and 1-N-methyl-2-pyrrolidinone (100 ml) is heated to 160° C. for 118 hours. The reaction mixture is cooled to room temperature and diluted with ether and water. The organic phase is separated and concentrated and the residue is purified by column chromatography (petrol ether:ethyl acetate, 95:5 v/v) yielding the pure product as white crystals, 1.3 g, (22%) having a melting point of 95-96° C.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customThe organic phase is separated
  3. concentrationconcentrated
  4. customthe residue is purified by column chromatography (petrol ether:ethyl acetate, 95:5 v/v)

Sources & evidence

ORD record
ord-ce0e17e919c2490d9f747aa244f6f4a0
Source dataset
uspto-grants-1999_12
Patent number
US06001883

Reaction notes

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