Phosphorus oxybromide → Ethyl 4-bromoquinoline-2-carboxylate

HRID 1430073

반응식

HRID 1430073 반응식
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

참가 물질

5

반응물 2

HCID 24613Phosphorus oxybromideHCID 178469285HCID 178469285, 화합물

생성물 1

HCID 21992780Ethyl 4-bromoquinoline-2-carboxylate

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6342Acetonitrile용매

실험 절차

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+.

후처리

  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

출처 및 근거

ORD 기록
ord-e09829a607c34573bc9003d8cc690a4b
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940765B2

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