Ammonia → 2-Bromo-1,10-phenanthroline

HRID 716557ノート

反応式

HRID 716557 の反応式
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

参加物

5

反応物 4

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

生成物 1

HCID 128302472-Bromo-1,10-phenanthroline収率 94%

反応条件

温度
80 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-cdc3fb9115ca4a39877736a18f2cf1f4
出典データセット
uspto-grants-2015_11
特許番号
US09187690B2

反応ノート

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