Sodium Carbonate → 3,3-dibromo-2-propenyl 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]benzoate

HRID 2248557Notes

Reaction equation

HRID 2248557 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]=[C:13]2[O:23][CH3:24])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:25][C:26]([Br:30])=[CH:27][CH2:28]Br.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:21])([F:20])[F:22])[N:14]=[C:13]2[O:23][CH3:24])=[CH:7][C:3]=1[C:4]([O:6][CH2:28][CH:27]=[C:26]([Br:30])[Br:25])=[O:5]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 130414871,1,3-Tribromoprop-1-eneHCID 197808272-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-benzoic acid

Product 1

HCID 199942463,3-dibromo-2-propenyl 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.5 g of 2-chloro-4-fluoro-5-[2methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-benzoic acid, 1.37 g of 1,1,3-tribromo-1-propene and 0.52 g of sodium carbonate in 50 ml of anhydrous acetone is heated for 8 hours while stirring. Subsequently, the insoluble constituents are filtered off under suction and the filtrate is evaporated to dryness under reduced pressure. The residue is dissolved in 100 ml of diethyl ether and the solution is extracted three times with 50 ml of water each time. The organic phase is then dried over anhydrous sodium sulphate and evaporated to dryness, and the residue is purified by chromatography on a silica gel column using n-hexane/diethyl ether (3:1) as the eluent. There is obtained 3,3-dibromo-2-propenyl 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]benzoate, 1H-NMR (CDCl3, 400 MHz): 7.89 ppm (d, 1H), 7.42 ppm (d, 1H), 6.72 ppm (t, 1H), 6.62 ppm (s. 1H), 4.82 ppm (d, 2H), 4.02 ppm (d, 3H).

Workup

  1. temperatureis heated for 8 hours
  2. filtrationSubsequently, the insoluble constituents are filtered off under suction
  3. customthe filtrate is evaporated to dryness under reduced pressure
  4. dissolutionThe residue is dissolved in 100 ml of diethyl ether
  5. extractionthe solution is extracted three times with 50 ml of water each time
  6. dry with materialThe organic phase is then dried over anhydrous sodium sulphate
  7. customevaporated to dryness
  8. customthe residue is purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-f5902b0d1115498a8b17dbc4bd9aa987
Source dataset
uspto-grants-1991_08
Patent number
US05041156

Reaction notes

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