Bromine → HCID 69155771, compound

HRID 750229Notes

Reaction equation

HRID 750229 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[Br:35]Br>ClCCl>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:25]=[CH:26][C:27]([OH:30])=[C:28]([Br:35])[CH:29]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:4]

Participants

5

Reactant 3

HCID 24408BromineHCID 6451240Aluminum(III) ChlorideHCID 69156619HCID 69156619, compound

Product 1

HCID 69155771HCID 69155771, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 6-bromo-2-(4-hydroxybenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (290 mg), aluminum chloride (82 mg) and dichloromethane (5.7 ml) was added bromine (39 μl) at 0° C. with stirring, and the mixture was stirred for 1 hr. After the completion of the reaction, the reaction mixture was washed with water, dried and concentrated. The residue was purified by medium pressure preparative LC (hexane/ethyl acetate=4/1-1/1) to give the title compound (180 mg) as colorless crystals.

Workup

  1. stirringthe mixture was stirred for 1 hr
  2. customAfter the completion of the reaction
  3. washthe reaction mixture was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by medium pressure preparative LC (hexane/ethyl acetate=4/1-1/1)

Sources & evidence

ORD record
ord-f1c0553f647e483b82b22698891c444c
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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