N-bromobutanimide → 6-(1-Bromoethyl)-4-oxo-4H-1-benzopyran-3-carbonitrile

HRID 2083226Notes

Reaction equation

HRID 2083226 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH:10]=[C:9]([C:12]#[N:13])[C:8](=[O:14])[C:7]=2[CH:15]=1)[CH3:2].C1C(=O)N([Br:23])C(=O)C1>ClC(Cl)(Cl)Cl>[Br:23][CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH:10]=[C:9]([C:12]#[N:13])[C:8](=[O:14])[C:7]=2[CH:15]=1)[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 51968426-ethyl-4-oxochromene-3-carbonitrile

Product 1

HCID 203582246-(1-Bromoethyl)-4-oxo-4H-1-benzopyran-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 9.95 parts of 6-ethyl-4-oxo-4H-1-benzopyran-3-carbonitrile 8.90 parts of NBS and 300 parts by volume of tetrachloromethane is refluxed under stirring and irradiation of infrared ray (100 volt, 375 WR) for 2 hours. The tetrachloromethane is distilled off and the solid residue is well shaken with 500 parts by volume of ethyl acetate and 100 parts by volume of water. The ethyl acetate layer is collected and shaken with 100 parts by volume of water. In this manner, the ethyl acetate layer is repeatedly washed with water until the solid residue disappears. The ethyl acetate layer is dried on Na2SO4, concentrated and cooled. The procedure yields 12.11 parts of 6-(1-bromoethyl)-4-oxo-4H-1-benzopyran-3-carbonitrile as colorless crystals. Melting point: 162-164° C

Workup

  1. temperatureis refluxed
  2. customirradiation of infrared ray (100 volt, 375 WR) for 2 hours
  3. distillationThe tetrachloromethane is distilled off
  4. stirringthe solid residue is well shaken with 500 parts by volume of ethyl acetate and 100 parts by volume of water
  5. customThe ethyl acetate layer is collected
  6. stirringshaken with 100 parts by volume of water
  7. washIn this manner, the ethyl acetate layer is repeatedly washed with water until the solid residue
  8. dry with materialThe ethyl acetate layer is dried on Na2SO4
  9. concentrationconcentrated
  10. temperaturecooled

Sources & evidence

ORD record
ord-f4599715fb634e5eb81ccfabdd09bf03
Source dataset
uspto-grants-1978_04
Patent number
US04085116

Reaction notes

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