Carbon tetrabromide → HCID 22731440, 화합물

HRID 1356723노트

반응식

HRID 1356723 반응식
[C:1]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([S:15]([C:18]1[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=1[CH3:26])(=[O:17])=[O:16])[CH:10]=[C:9]2[CH3:27])(OCC)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:54]>C1COCC1.C(OCC)(=O)C>[Br:54][CH2:1][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([S:15]([C:18]1[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=1[CH3:26])(=[O:17])=[O:16])[CH:10]=[C:9]2[CH3:27]

참가 물질

7

반응물 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 21226445Aluminium lithium hydrideHCID 22731441HCID 22731441, 화합물

생성물 1

HCID 22731440HCID 22731440, 화합물수율 94%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Under cooling with ice, 5-carboethoxy-3-methyl-1-(2,4,6-trimethylbenzenesulfonyl)indole (1.13 g, 2.94 mmol) was added to a solution of lithium aluminum hydride (223 mg, 5.88 mmol) in THF (10 ml), followed by stirring for 1 hour. The reaction mixture was mixed with ethyl acetate and a 2N aqueous HCl solution and extracted with chloroform. The organic layer was washed with water and saturated brine, dried over magnesium sulfate and evaporated to remove the solvent. The thus obtained residue was dissolved in methylene chloride (20 ml) and mixed with triphenylphosphine (1.06 g, 4.04 mmol) and carbon tetrabromide (1.34 g, 4.04 mmol) under cooling with ice, followed by stirring for 1 hour. The reaction mixture was evaporated to remove the solvent; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:5) to give the titled compound (1.12 g, 94%).

후처리

  1. extractiona 2N aqueous HCl solution and extracted with chloroform
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto remove the solvent
  6. dissolutionThe thus obtained residue was dissolved in methylene chloride (20 ml)
  7. temperatureunder cooling with ice
  8. stirringby stirring for 1 hour
  9. customThe reaction mixture was evaporated
  10. customto remove the solvent

출처 및 근거

ORD 기록
ord-b73931a0d1a547169b61cc75e3ae43ad
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586630B1

반응 노트

불러오는 중…