Phosphorus oxybromide → Ethyl 4-bromoquinoline-2-carboxylate

HRID 1430073ノート

反応式

HRID 1430073 の反応式
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:3]=1.P(Br)(Br)([Br:19])=O>C1(C)C=CC=CC=1.C(#N)C>[Br:19][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:3]=1

参加物

5

反応物 2

HCID 24613Phosphorus oxybromideHCID 178469285HCID 178469285、化合物

生成物 1

HCID 21992780Ethyl 4-bromoquinoline-2-carboxylate

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6342Acetonitrile溶媒

実験手順

A solution of ethyl 4-hydroxyquinoline-2-carboxylate (10.0 g, 46.0 mmol) and phosphorus oxybromide (13.2 g, 46.0 mmol) in 100 mL of toluene and 10.0 mL acetonitrile was heated at 75° C. for 1.5 h. The reaction mixture was cooled to room temperature, quenched slowly with water, and extracted with ethyl acetate. The organic fraction was washed with brine, dried over sodium sulfate, filtered, and concentrated. The resultant residue was subjected to silica gel chromatography eluting with 0-50% ethyl acetate in hexanes to afford ethyl 4-bromoquinoline-2-carboxylate that gave a mass ion (ES+) of 280.1 (79Br) for M+H+.

後処理

  1. customquenched slowly with water
  2. extractionextracted with ethyl acetate
  3. washThe organic fraction was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washeluting with 0-50% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-e09829a607c34573bc9003d8cc690a4b
出典データセット
uspto-grants-2015_01
特許番号
US08940765B2

反応ノート

読み込み中…