Hydrogen Bromide → HCID 19752458, compound

HRID 483353Notes

Reaction equation

HRID 483353 reaction equation
N[C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[BrH:11].N([O-])=O.[Na+].[C:16]([O:20][CH2:21][CH3:22])(=[O:19])[CH:17]=[CH2:18]>CC(C)=O.[Cu-]=O.O>[Br:11][CH:17]([CH2:18][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8](=[O:10])[CH3:9])[CH:3]=1)[C:16]([O:20][CH2:21][CH3:22])=[O:19]

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 74173'-AminoacetophenoneHCID 8821Ethyl AcrylateHCID 23668193Sodium Nitrite

Product 1

HCID 19752458HCID 19752458, compound

Reagents, catalysts & solvents 3

HCID 178419072HCID 178419072, compoundCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

solution of 5 g of m-aminoacetophenone in 100 ml of acetone was combined with 25 ml of water and 15 ml of 47% hydrobromic acid and the resultant mixture was stirred for 30 minutes with 10 ml of an aqueous solution containing 3.32 g of sodium nitrite added dropwise in advance thereto at 5 C. The produced reaction solution and 28 ml of ethyl acrylate added dropwise thereto and 0.53 g of copper (I) oxide added piecemeal thereto at 40° C. were stirred for 2 hours. The resultant mixture was combined with water, extracted with ethyl acetate An organic layer was washed with water and a saturated aqueous saline solution, dried with anhydrous magnesium sulfate, and distilled under a vacuum to expel the solvent to obtain ethyl 2-bromo-3-(3-acetylphenyl)propionate.

Workup

  1. additionadded dropwise in advance
  2. additionadded dropwise
  3. extractionextracted with ethyl acetate An organic layer
  4. washwas washed with water
  5. dry with materiala saturated aqueous saline solution, dried with anhydrous magnesium sulfate
  6. distillationdistilled under a vacuum

Sources & evidence

ORD record
ord-7b4f8c42917c4c74a0af40604cd5fc68
Source dataset
uspto-grants-1993_07
Patent number
US05225426

Reaction notes

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