Sodium Carbonate → Ethyl 2-(3,4-dimethoxyphenyl)-4-(trifluoromethyl)benzoate

HRID 439547Notes

Reaction equation

HRID 439547 reaction equation
Br[C:2]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:17][O:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:24]=1[O:25][CH3:26].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([C:2]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:22]=[CH:23][C:24]=1[O:25][CH3:26]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27347023,4-Dimethoxyphenylboronic acidHCID 15766264Ethyl 2-bromo-4-(trifluoromethyl)benzoate

Product 1

HCID 15766263Ethyl 2-(3,4-dimethoxyphenyl)-4-(trifluoromethyl)benzoateYield 94%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

263 g (0.885 mol) of ethyl 2-bromo-4-(trifluoromethyl)benzoate, 750 ml of 1,2-dimethoxyethane, 4 g of tetrakis(triphenylphosphine)palladium, 177 g (0.974 mol) of 3,4-dimethoxyphenylboronic acid and 1000 ml of a 2M aqueous sodium carbonate solution are introduced successively, under an inert atmosphere, into a four-liter round-bottomed flask. The reaction mixture is brought to reflux for fourteen hours and then evaporated to a third under reduced pressure. The reaction mixture is poured onto two liters of water; the precipitate which forms is filtered on sintered glass, rinsed with water and then dried under a stream of air. There is thus obtained 294 g (yield: 94%) of ethyl 2-(3,4-dimethoxyphenyl)-4-(trifluoromethyl)benzoate in the form of a beige solid melting at 89° C.

Workup

  1. temperatureto reflux for fourteen hours
  2. customevaporated to a third under reduced pressure
  3. additionThe reaction mixture is poured onto two liters of water
  4. filtrationthe precipitate which forms is filtered on sintered glass
  5. washrinsed with water
  6. customdried under a stream of air

Sources & evidence

ORD record
ord-9e3d5b86151442e4a0337e966a23226f
Source dataset
uspto-grants-1996_05
Patent number
US05514719

Reaction notes

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