Hydrogen Bromide → HCID 14684949, compound

HRID 1701337Notes

Reaction equation

HRID 1701337 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1N.N([O-])=O.[Na+].[C:13]([O:17][CH3:18])(=[O:16])[CH:14]=[CH2:15].[BrH:19]>CC(C)=O.O>[Br:19][CH:14]([CH2:15][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[Cl:1])[C:13]([O:17][CH3:18])=[O:16]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 72402-ChloroanilineHCID 7294Methyl AcrylateHCID 23668193Sodium Nitrite

Product 1

HCID 14684949HCID 14684949, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

6.35 g. of 2-chloroaniline (0.05 mole) in acetone (100 ml.) and concentrated hydrobromic acid (16 ml.) was stirred at -5° C. and treated with a solution of 4.2 g. of sodium nitrite (0.06 mole) in water (10 ml.). Methyl acrylate (0.5 mole) (43 g.) and cuprous bromide (100 mg.) were then added at 0° C. The reaction temperature was kept below 15° C. until nitrogen evolution ceased and then stirred at 25° C. for thirty minutes. The reaction mixture was poured into water and extracted with benzene which was dried over sodium sulfate and evaporated to give methyl 2-bromo-3-(2-chlorophenyl)propionate.

Workup

  1. additiontreated with a solution of 4.2 g
  2. customwas kept below 15° C. until nitrogen evolution
  3. extractionextracted with benzene which
  4. dry with materialwas dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-1ff139c7bc944b8b8c5d9e1984bb9c85
Source dataset
uspto-grants-1980_03
Patent number
US04192888

Reaction notes

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