Bromine → HCID 70416401, compound

HRID 980796Notes

Reaction equation

HRID 980796 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:14])[C:12]#[N:13])=[CH:7][CH:6]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[Br:1][C:6]1[CH:7]=[C:8]([CH:11]([CH3:14])[C:12]#[N:13])[CH:9]=[CH:10][C:5]=1[O:4][CH3:3]

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 122976702-(4-Methoxyphenyl)propanenitrile

Product 1

HCID 70416401HCID 70416401, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (21.4 ml) is added dropwise over a period of 1 hour to a stirred solution of 4-methoxyphenylpropionitrile (67.5 g) and sodium acetate (68.4 g) in glacial acetic acid (420 ml). The reaction mixture is stirred for an additional 30 minutes and partitioned between water and ether. The ether layer is washed with sodium carbonate solution, 10% aqueous NaOH, saturated salt, dried over Na2SO4 and filtered. The filtrate is evaporated in vacuo yielding the desired product, B.P. 155°-158° C. (4 mm).

Workup

  1. custompartitioned between water and ether
  2. washThe ether layer is washed with sodium carbonate solution, 10% aqueous NaOH, saturated salt
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-b46d7cdfbc4e4cf097f187535abc4121
Source dataset
uspto-grants-1987_01
Patent number
US04639442

Reaction notes

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