2,4-Dinitrobenzenesulfonic acid → HCID 11236711, compound

HRID 1098584Notes

Reaction equation

HRID 1098584 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[S:13]([OH:16])(=[O:15])=[O:14])([O-:3])=[O:2].C(O)(=[O:19])C.C(O)(=O)C.[I:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CC#N>[OH:19][I:25]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[O:14][S:13]([C:5]1[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 69592,4-Dinitrobenzenesulfonic acidHCID 12217721Iodo benzene diacetate

Product 1

HCID 11236711HCID 11236711, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2,4-dinitrobenzenesulfonic acid (16.5 g, 62.0 mmol) in minimum quantity of CH3CN was added at once to a translucent solution of iodobenzene diacetate (10 g, 31.0 mmol) in CH3CN (100 mL). The reaction mixture was stirred for 1 hour at RT. The solution was chilled in ice and then the solution was kept in freezer. The solid was filtered and washed with Et2O to obtain [hydroxy(2,4-dinitrobenzenesulfonyloxy)iodo]benzene (HDNIB) (13.9 g, 96% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.91 (brs, 1H), 8.71 (d, J=2.4 Hz, 1H), 8.56 (dd, J=2.0, and 8.4 Hz, 1H), 8.38 (m, 2H), 8.24 (d, J=8.4 Hz, 1H), 7.88 (m, 1H), 7.77 (m, 2H).

Workup

  1. temperatureThe solution was chilled in ice
  2. filtrationThe solid was filtered
  3. washwashed with Et2O

Sources & evidence

ORD record
ord-d19228f93f7a476bb874eff6fe29c37f
Source dataset
uspto-grants-2012_03
Patent number
US08143293B2

Reaction notes

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