Iodine → 5-Bromo-2-iodobenzonitrile

HRID 468717Notes

Reaction equation

HRID 468717 reaction equation
N[C:2]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[C:4]#[N:5].N(OC(C)(C)C)=O.[I:18]I.[O-]S([O-])=O.[Na+].[Na+]>C(#N)C>[Br:10][C:7]1[CH:8]=[CH:9][C:2]([I:18])=[C:3]([CH:6]=1)[C:4]#[N:5]

Participants

6

Reactant 4

HCID 807IodineHCID 10906Tert-Butyl nitriteHCID 24437Sodium SulfiteHCID 4297402-Amino-5-bromobenzonitrile

Product 1

HCID 70208745-Bromo-2-iodobenzonitrileYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-amino-5-bromobenzonitrile (100 g, 0.5 mol) was added during 1 hour to tert-butyl nitrite (117 mL, 0.75 mol) and iodine (250 g, 1.1 mol) in dry acetonitrile (600 mL) under nitrogen while maintaining the temperature between 30° C. and 35° C. Stirring was continued for 60 minutes at 23° C. Subsequent addition of saturated aqueous Na2SO3 (2 L) gave precipitate which was collected by filtration, and washed with hexanes to obtain 100 g (65%) of 5-bromo-2-iodobenzonitrile. 1H NMR (400 MHz, DMSO-d6) δ 8.14 (d, J=2.4 Hz, 1H), 7.95 (d, J=8.4 Hz, 1H), 7.64 (dd, J=2.4, 8.4 Hz, 1H).

Workup

  1. temperaturewhile maintaining the temperature between 30° C. and 35° C
  2. customgave precipitate which
  3. filtrationwas collected by filtration
  4. washwashed with hexanes

Sources & evidence

ORD record
ord-bfe39bd479874e7bbd59b41f5c7fa124
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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