Bromine → 4-bromo-5,6,7,8-tetrahydro-1(2H)-Isoquinolinone

HRID 1713397Notes

Reaction equation

HRID 1713397 reaction equation
[C:1]1(=[O:11])[C:10]2[CH:5]([CH2:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.[Br:12]Br.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[Br:12][C:4]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:1](=[O:11])[NH:2][CH:3]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 66591041HCID 66591041, compound2×

Product 1

HCID 594638144-bromo-5,6,7,8-tetrahydro-1(2H)-IsoquinolinoneYield 96.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

32.4 g (217 mmol) of tetrahydroisoquinolinone (compound 5) is dissolved in 300 ml of chloroform at 5° C. and then 11.2 ml (34.7 g, 217 mmol) of bromine, dissolved in 150 ml of chloroform, are added dropwise over the course of 1 h. The mixture is stirred while cooling in ice for a further hour and then neutralized with 150 ml of saturated NaHCO3 solution and filtered with suction. The organic phase of the filtrate is extracted with dichloromethane and concentrated. The residue is mixed with ethyl acetate, filtered off with suction and dried together with the first residue in a vacuum drying oven at 45° C. 47.7 g (96%) of colorless bromide are obtained.

Workup

  1. additionare added dropwise over the course of 1 h
  2. temperaturewhile cooling in ice for a further hour
  3. filtrationfiltered with suction
  4. extractionThe organic phase of the filtrate is extracted with dichloromethane
  5. concentrationconcentrated
  6. additionThe residue is mixed with ethyl acetate
  7. filtrationfiltered off with suction
  8. customdried together with the first residue in a vacuum
  9. customdrying oven at 45° C

Sources & evidence

ORD record
ord-3db7efe3e18e47fab619b84bcd5d9e40
Source dataset
uspto-grants-2010_09
Patent number
US07795278B2

Reaction notes

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