Hydrochloric Acid → HCID 20462998, compound

HRID 325861Notes

Reaction equation

HRID 325861 reaction equation
[C:1]([C:3](=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[F:17][C:18]1[CH:23]=[CH:22][C:21]([Mg]Br)=[CH:20][CH:19]=1.BrC1C=CC(F)=CC=1.[Mg].Cl>C1(C)C=CC=CC=1.CCOCC>[C:1]([CH:3]([CH:9]([C:21]1[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=1)[C:10]1[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 99931-Bromo-4-fluorobenzeneHCID 367490α-Cyano-4-methylbenzeneacrylic acid ethyl esterHCID 5462224MagnesiumHCID 178418676HCID 178418676, compound

Product 1

HCID 20462998HCID 20462998, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 860 grams of ethyl α-cyano-4-methylcinnamate in 1500 milliliters of hot toluene was added to a solution of 4-fluorophenyl magnesium bromide prepared from 860 grams of 4-bromofluorobenzene and 130 grams of magnesium turnings in 2500 milliliters of ether, under simultaneous distillation of the ether, until a final temperature of 80 degrees Centigrade was reached in the reaction mixture. The reaction mixture was then refluxed for 1 hour, whereupon it was hydrolysed with ice and 450 milliliters of concentrated hydrochloric acid. The mixture was then extracted with ether, washed with water, dried over anhydrous magnesium sulfate, treated with active carbon and evaporated in vacuo to give 1275 grams of crude ethyl α-cyano-3-(p-fluorophenyl)-3-(p-tolyl)-propionate.

Workup

  1. customtemperature of 80 degrees Centigrade
  2. temperatureThe reaction mixture was then refluxed for 1 hour, whereupon it
  3. extractionThe mixture was then extracted with ether
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. additiontreated with active carbon
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-4897378b147048769a45277880ecb66c
Source dataset
uspto-grants-1984_04
Patent number
US04443448

Reaction notes

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