Phosphorus oxide (P4O10) → 5-Bromo-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline

HRID 445368노트

반응식

HRID 445368 반응식
[Br:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][CH2:5][NH:6][C:7](=O)[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:3]=1[CH2:4][CH2:5][N:6]=[C:7]2[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1

참가 물질

4

반응물 2

HCID 14812Phosphorus oxide (P4O10)HCID 59536435N-(2-bromophenethyl)-4-(trifluoromethyl)benzamide

생성물 1

HCID 595362925-Bromo-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a 100 mL round-bottomed flask was added N-(2-bromophenethyl)-4-(tri-fluoromethyl)benzamide (1.6 g, 4299 μmol, from step 1), toluene (50 mL), phosphorus pentaoxide (1061 μL, 17196 μmol, Aldrich). The reaction mixture was stirred at reflux for 5 h. The mixture was cooled down and then poured into ice (ca 50 g), and extracted with EtOAc (2×50 mL). The organic extract was washed with water (30 mL), saturated NaCl (30 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 10% EtOAc/hexanes to give 5-bromo-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline. MS (ESI pos. ion) m/z: 354 (M+1).

후처리

  1. temperatureat reflux for 5 h
  2. temperatureThe mixture was cooled down
  3. extractionextracted with EtOAc (2×50 mL)
  4. extractionThe organic extract
  5. washwas washed with water (30 mL), saturated NaCl (30 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customthe residue was purified by silica gel chromatography
  10. washeluting with 10% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-c47b01e7b74c4b0cb3d7092c5523950d
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476297B2

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