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

HRID 262093

반응식

HRID 262093 반응식
[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

참가 물질

7

반응물 5

HCID 807IodineHCID 209033-Cyclohexene-1-carboxylic acid2회HCID 24477Sodium ThiosulfateHCID 25352Nitrogen oxide (N2O4)2회HCID 213199065-Cyanomethyl-2,7-dibromo-3-phenylbenzofuran

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fb0bd4904a8842a48622e57779dcca46
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04153619

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