Bromine → HCID 20445749, compound

HRID 2418153Notes

Reaction equation

HRID 2418153 reaction equation
[O:1]([C:8]1[CH:23]=[CH:22][C:11]([C:12]([CH2:14][CH2:15][C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])=[O:13])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[Br:28]Br>C(Cl)(Cl)Cl>[Br:28][CH:14]([C:12](=[O:13])[C:11]1[CH:22]=[CH:23][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:9][CH:10]=1)[CH2:15][C:16]([O:18][CH:19]([CH3:20])[CH3:21])=[O:17]

Participants

5

Reactant 3

HCID 24408BromineHCID 6451240Aluminum(III) ChlorideHCID 20445752HCID 20445752, compound

Product 1

HCID 20445749HCID 20445749, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

6.24 g of isopropyl 3-(4-phenoxybenzoyl)propionate were dissolved in 50 ml of chloroform. After a catalytic amount of anhydrous aluminum chloride was added, a solution of 3.62 g of bromine in 20 ml of chloroform was added dropwise over 30 minutes. The reaction mixture was washed with water, then dried over magnesium sulfate. The chloroform was removed by evaporation under reduced pressure to give oily isopropyl 3-bromo-3-(4-phenoxybenzoyl)propionate, which was dissolved, without purification, in 50 ml of dimethylformamide. 3.02 g of potassium acetate were added under ice-cooling, and the mixture was stirred for 30 minutes. Diethyl ether was added to the reaction mixture, which was then washed with water and dried over magnesium sulfate. The diethyl ether was distilled off under reduced pressure and the residue was recrystallized from a mixture of hexane and diethyl ether to give 5.83 g of isopropyl 3-(4-phenoxybenzoyl)acrylate.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried over magnesium sulfate
  3. customThe chloroform was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-6c8f5274ad4a4524a4acf2cff469cb37
Source dataset
uspto-grants-1984_09
Patent number
US04472316

Reaction notes

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