1,2-Dichlorobenzene → 1-(2-Bromophenyl)isoquinoline

HRID 84130Notes

Reaction equation

HRID 84130 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][N:9]=1.ClC1C=CC=CC=1Cl>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][N:9]=1

Participants

5

Reactant 2

HCID 72391,2-DichlorobenzeneHCID 107795371-(2-Bromophenyl)-3,4-dihydroisoquinoline

Product 1

HCID 114033581-(2-Bromophenyl)isoquinoline

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 28.6 g (100 mmol) of 1-(2-bromophenyl)-3,4-dihydroisoquinoline, 86.9 g (1 mol) of manganese dioxide and 200 ml of 1,2-dichlorobenzene was stirred at 180° C. for 5 h. After cooling, the mixture was diluted with 500 ml of toluene and filtered through silica gel. After the solvent had been removed, the product was obtained as a yellow oil. The yield at a purity of approx. 99.0% was 26.0 g (91 mmol), 91.4% of theory.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered through silica gel
  3. customAfter the solvent had been removed
  4. customthe product was obtained as a yellow oil
  5. customThe yield at a purity of approx. 99.0%

Sources & evidence

ORD record
ord-8514b59627a04518b144b82635f15de2
Source dataset
uspto-grants-2014_09
Patent number
US08846920B2

Reaction notes

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