Formaldehyde → 1-(5-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone

HRID 1444690Notes

Reaction equation

HRID 1444690 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][CH2:5][NH:6][C:7](=[O:12])[C:8]([F:11])([F:10])[F:9].[CH2:17]=O.S(=O)(=O)(O)O>C(O)(=O)C>[Br:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:3]=1[CH2:4][CH2:5][N:6]([C:7](=[O:12])[C:8]([F:10])([F:11])[F:9])[CH2:17]2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 58597272N-[2-(2-bromophenyl)ethyl]-2,2,2-trifluoroacetamide

Product 1

HCID 184142741-(5-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of N-(2-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 of 1-(5-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-91c733e64ffa4af6a73083e7ba815cb4
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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