Ammonia → 2-Bromo-1,10-phenanthroline

HRID 716557

반응식

HRID 716557 반응식
C[N:2]1[C:15]2[C:6](=[CH:7][CH:8]=[C:9]3[C:14]=2[N:13]=[CH:12][CH:11]=[CH:10]3)[CH:5]=[CH:4][C:3]1=O.P(Br)(Br)(Br)(Br)[Br:18].P(Br)(Br)(Br)=O.N>>[Br:18][C:3]1[CH:4]=[CH:5][C:6]2[C:15](=[C:14]3[C:9](=[CH:8][CH:7]=2)[CH:10]=[CH:11][CH:12]=[N:13]3)[N:2]=1

참가 물질

5

반응물 4

HCID 222AmmoniaHCID 24613Phosphorus oxybromideHCID 62678Phosphorus pentabromideHCID 35813871-Methyl-1,10-phenanthrolin-2(1H)-one

생성물 1

HCID 128302472-Bromo-1,10-phenanthroline수율 94%

반응 조건

온도
80 °C

실험 절차

Under a stream of argon, to compound (2) (10 g; 47.6 mmol), phosphorus pentabromide (28 g; 65 mmol) and phosphorus oxybromide (50 g; 174 mmol) were added at room temperature. The reaction temperature was raised to 80° C. and the reaction mixture was stirred for 6 hours. The reaction mixture was cooled in an ice bath, and then poured into ice water. Concentrated aqueous ammonia was added thereto and the resulting mixture was made alkaline. The reaction mixture was extracted with chloroform, and the organic layer thus obtained was washed with water, dried over sodium sulfate, and then evaporated under reduced pressure. The resulting residue was separated and purified by silica gel column chromatography (Si02, 250 g) (toluene/ethyl acetate=5/1 to 3/1 to 1/1 to ethyl acetate), to give 6.9 g (yield: 94%) of the title compound (7).

후처리

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. extractionThe reaction mixture was extracted with chloroform
  3. customthe organic layer thus obtained
  4. washwas washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe resulting residue was separated
  8. custompurified by silica gel column chromatography (Si02, 250 g) (toluene/ethyl acetate=5/1 to 3/1 to 1/1 to ethyl acetate)

출처 및 근거

ORD 기록
ord-cdc3fb9115ca4a39877736a18f2cf1f4
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187690B2

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