Allyl bromide → HCID 12895736, compound

HRID 1680212Notes

Reaction equation

HRID 1680212 reaction equation
[CH2:1]([Mg]Br)[CH:2]=[CH2:3].C(Br)C=C.[Cl:10][C:11]1[S:15][C:14]([CH2:16]Cl)=[CH:13][CH:12]=1>CCOCC>[Cl:10][C:11]1[S:15][C:14]([CH2:16][CH2:3][CH:2]=[CH2:1])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 5830792-Chloro-5-(chloromethyl)thiopheneHCID 178455850HCID 178455850, compound

Product 1

HCID 12895736HCID 12895736, compoundYield 195.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of allyl magnesium bromide (from 14.6 g of magnesium and 24.2 g (0.2 M) of allyl bromide) in 100 ml ether is added dropwise with stirring to 29.9 g of 5-chloro-2-chloromethylthiophene in 10 ml ether over half an hour and the resulting mixture heated under reflux overnight. The mixture is then poured into 300 ml ice cold dilute sulfuric acid, the ether layer separated and the aqueous phase extracted with 200 ml of ether. The combined ethereal solutions are washed with aqueous potassium carbonate, dried over MgSO4 and evaporated to give crude 4-(5-chloro-2-thienyl)-1-butene as a yellow oil (34 g).

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureunder reflux overnight
  3. customthe ether layer separated
  4. extractionthe aqueous phase extracted with 200 ml of ether
  5. washThe combined ethereal solutions are washed with aqueous potassium carbonate
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-11bf73e510b5456ba3a8bad29c96dd32
Source dataset
uspto-grants-1981_06
Patent number
US04272545

Reaction notes

Loading…