Boron tribromide → HCID 10275168, compound

HRID 218573Notes

Reaction equation

HRID 218573 reaction equation
[CH3:1][N:2]([CH3:34])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]([C:25]2[CH:30]=[CH:29][C:28]([CH:31]([CH3:33])[CH3:32])=[CH:27][CH:26]=2)[C:11]([CH:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23]C)[CH:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:1][N:2]([CH3:34])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]([C:25]2[CH:26]=[CH:27][C:28]([CH:31]([CH3:32])[CH3:33])=[CH:29][CH:30]=2)[C:11]([CH:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([OH:23])[CH:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 5311122HCID 5311122, compound

Product 1

HCID 10275168HCID 10275168, compoundYield 11.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[(4-Dimethylaminophenyl)methyl]-N-(4-isopropylphenyl)-7-methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxamide (3.2 g) was dissolved in methylene chloride (60 mL), and boron tribromide (0.72 mL) was added under ice-cooling. The mixture was stirred at room temperature for one day. The reaction mixture was partitioned between saturated aqueous sodium hydrogencarbonate and chloroform. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give N-[(4-dimethylaminophenyl)methyl]-7-hydroxy-N-(4-isopropylphenyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.36 g). melting point: 214-217° C.

Workup

  1. temperaturecooling
  2. customThe reaction mixture was partitioned between saturated aqueous sodium hydrogencarbonate and chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-397a0bc5f15c45039ada242355125c30
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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