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

HRID 445368Notes

Reaction equation

HRID 445368 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c47b01e7b74c4b0cb3d7092c5523950d
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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