Bromine → HCID 57423043, compound

HRID 249960Notes

Reaction equation

HRID 249960 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Br:13]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCOCC1>[NH2:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([Br:13])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 111478972-Amino-4-nitrobenzonitrile

Product 1

HCID 57423043HCID 57423043, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

2-Amino-4-nitrobenzonitrile (1.6 g, 9.81 mmol) is presented as an initial charge in 30 mL of dioxane and is mixed at 10° C. with bromine (0.56 mL, 11 mmol). This is followed by stirring at 60° C. for 6 hours. After cooling to room temperature, the batch is added to dilute sodium thiosulphate solution. After extraction of dichloromethane, the combined organic phases are dried over sodium sulphate to leave, after removal of the solvent and chromatographic purification (silica gel, n-hexane/ethyl acetate: 0→100% ethyl acetate), the product in 36% yield (820 mg).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionAfter extraction of dichloromethane
  3. dry with materialthe combined organic phases are dried over sodium sulphate
  4. customto leave
  5. customafter removal of the solvent and chromatographic purification (silica gel, n-hexane/ethyl acetate: 0→100% ethyl acetate)

Sources & evidence

ORD record
ord-b9a5937cd98e47a68b97f74cd27c51cb
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

Loading…