Formaldehyde → 1-(7-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone

HRID 1444696Notes

Reaction equation

HRID 1444696 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])=[CH:4][CH:3]=1.[CH2:17]=O.S(=O)(=O)(O)O>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH2:6][CH2:7][N:8]([C:9](=[O:14])[C:10]([F:12])([F:13])[F:11])[CH2:17]2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 1518036N-(4-Bromophenethyl)-2,2,2-trifluoroacetamide

Product 1

HCID 109688311-(7-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of N-(4-bromophenethyl)-2,2,2-trifluoroacetamide (8.88 g, 30 mmol) and paraformaldehyde (13.5 g, 0.45 mol) in 45 mL of glacial acetic acid at room temperature was slowly added 30 mL of sulfuric acid (96.6%). After stirring at room temperature overnight, the reaction mixture was quenched with ice water and extracted with EtOAc, washed with brine and Sat. NaHCO3 and dried over Na2SO4. After concentration, flash chomatography (SiO2, hexane/DCM=1:1) gave 1-(7-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone as a white solid.

Workup

  1. customthe reaction mixture was quenched with ice water
  2. extractionextracted with EtOAc
  3. washwashed with brine and Sat. NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentration, flash chomatography (SiO2, hexane/DCM=1:1)

Sources & evidence

ORD record
ord-a0b831cc002043cebf0c77d21abc342c
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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