Hydrochloric Acid → Ethyl 4-(2'-fluoro-4-biphenylyl)-4-oxo-butyrate

HRID 1973474Notes

Reaction equation

HRID 1973474 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[C:19]([O:26][CH2:27][CH3:28])(=[O:25])[CH2:20][CH2:21][C:22]([O-])=[O:23].Cl>CCOCC.C(Cl)CCl>[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:13]=[CH:14][C:15]([C:22](=[O:23])[CH2:21][CH2:20][C:19]([O:26][CH2:27][CH3:28])=[O:25])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 675792-FluorobiphenylHCID 6451240Aluminum(III) ChlorideHCID 18404837Monoethyl succinate chloride

Product 1

HCID 21437951Ethyl 4-(2'-fluoro-4-biphenylyl)-4-oxo-butyrateYield 77%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

26.6 gm (0.2 mol) of powdered aluminum chloride were introduced over a period of 15 minutes into a mixture consisting of 17.2 gm (0.1 mol) of 2-fluoro-biphenyl, 16.4 gm (0.1 mol) of ethyl succinate chloride and 200 ml of ethylene chloride at 10° C, accompanied by stirring, and the resulting mixture was heated for 3 hours at 60° C. Thereafter, the reaction mixture was allowed to stand for several hours at room temperature, was then poured into a mixture of ice and hydrochloric acid, and 200 ml of ether were added to the mixture. The organic phase was separated, washed with water, with aqueous sodium bicarbonate and again with water, dried over sodium sulfate, and the solvent was distilled off. The oily residue was distilled in vacuo, yielding 23.1 gm (77% of theory) of ethyl 4-(2'-fluoro-4-biphenylyl)-4-oxo-butyrate, b.p. 190°-192° C at 0.4 mm Hg, which solidified into a crystalline substance after standing for some time and had a melting point of 56°-58° C after recrystallization from petroleum ether.

Workup

  1. waitto stand for several hours at room temperature
  2. additionwere added to the mixture
  3. customThe organic phase was separated
  4. washwashed with water, with aqueous sodium bicarbonate and again with water
  5. dry with materialdried over sodium sulfate
  6. distillationthe solvent was distilled off
  7. distillationThe oily residue was distilled in vacuo

Sources & evidence

ORD record
ord-79ee2bbd16c14bb2a7cce967a6c5e926
Source dataset
uspto-grants-1976_12
Patent number
US03997589

Reaction notes

Loading…