Ethyl 4-bromocrotonate → HCID 46344355, compound

HRID 1078565Notes

Reaction equation

HRID 1078565 reaction equation
[Na].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([OH:16])=[C:7]([NH:9][C:10](=O)[C:11](F)(F)F)[CH:8]=1.BrCC=[CH:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(O)C>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[O:16][CH2:11][CH:10]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[NH:9][C:7]=2[CH:8]=1

Participants

5

Reactant 3

HCID 98102Ethyl 4-bromocrotonateHCID 5360545SodiumHCID 13278500HCID 13278500, compound

Product 1

HCID 46344355HCID 46344355, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

420 ml of ethanol are introduced into a 3 litre reactor, with magnetic stirring, cooled to 0° C., and 3.8 g (0.166 mol) of sodium are added slowly, in small portions, followed by successive and dropwise addition of 40 g (0.166 mol) of N-(5-chloro-2-hydroxyphenyl)trifluoroacetamide and 40 g (0.155 mol) of 75% pure ethyl 4-bromo-2-butenoate, and the mixture is heated at 85° C. for 2 hours. The solvent is evaporated off and the residue is taken up in 100 ml of water and 40 ml of 1N sodium hydroxide and extracted with diethyl ether. The organic phase is separated out, washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and evaporated. 28.58 g of product are obtained, which product is purified by chromatography on a column of silica gel, eluting with a cyclohexane/isopropyl ether (1/1 ratio) mixture.

Workup

  1. temperaturethe mixture is heated at 85° C. for 2 hours
  2. customThe solvent is evaporated off
  3. extraction40 ml of 1N sodium hydroxide and extracted with diethyl ether
  4. customThe organic phase is separated out
  5. washwashed with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-ed601e5b849d40688f683625764c0084
Source dataset
uspto-grants-1996_08
Patent number
US05550125

Reaction notes

Loading…