Iodine → 7-Bromo-5-cyanomethyl-2-nitro-3-phenylbenzofuran

HRID 262093Notes

Reaction equation

HRID 262093 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([Br:20])[C:7]2[O:11][C:10](Br)=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8]=2[CH:19]=1)#[N:2].[N+:21]([O-:26])([N+]([O-])=O)=[O:22].C1CCC(C(O)=O)CC=1.II.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[Br:20][C:6]1[C:7]2[O:11][C:10]([N+:21]([O-:26])=[O:22])=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8]=2[CH:19]=[C:4]([CH2:3][C:1]#[N:2])[CH:5]=1

Participants

7

Reactant 5

HCID 807IodineHCID 209033-Cyclohexene-1-carboxylic acid2×HCID 24477Sodium ThiosulfateHCID 25352Nitrogen oxide (N2O4)2×HCID 213199065-Cyanomethyl-2,7-dibromo-3-phenylbenzofuran

Product 1

HCID 213199467-Bromo-5-cyanomethyl-2-nitro-3-phenylbenzofuran

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution containing 11.1 g. (0.028 mole) of 5-cyanomethyl-2,7-dibromo-3-phenylbenzofuran, 10.7 g. (0.11 mole) of dinitrogen tetroxide, 13.9 g. (0.11 mole) of cyclohexene-4-carboxylic acid and 1 g. of iodine in 500 ml. of chloroform is stirred at room temperature for 16 hours. An additional 13.9 g. of cyclohexene-4-carboxylic acid and 10.7 g. of dinitrogen tetroxide are added, and stirring is continued for 16 hours. The reaction is then treated with 500 ml. of 10 percent sodium thiosulfate. The phases are separated, and the organic phase is washed thrice with 250 ml. portions of saturated sodium bicarbonate, once with 250 ml. of 3 N hydrochloric acid and dried. Evaporation gives 7-bromo-5-cyanomethyl-2-nitro-3-phenylbenzofuran as a yellow solid, recrystallized from ethyl acetate-hexane to give a sample for analysis.

Workup

  1. additionA solution containing 11.1 g
  2. additionThe reaction is then treated with 500 ml
  3. customThe phases are separated
  4. washthe organic phase is washed thrice with 250 ml
  5. dry with materialof 3 N hydrochloric acid and dried
  6. customEvaporation

Sources & evidence

ORD record
ord-fb0bd4904a8842a48622e57779dcca46
Source dataset
uspto-grants-1979_05
Patent number
US04153619

Reaction notes

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