Lithium Carbonate → HCID 86761409, compound

HRID 909385Notes

Reaction equation

HRID 909385 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:11])[C:9]=1[OH:10])[CH:5]=[O:6].[N+:12]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1)([O-:14])=[O:13].C(=O)([O-])[O-].[Li+].[Li+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:11])[C:9]=1[O:10][CH2:19][C:18]1[CH:21]=[CH:22][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=1)[CH:5]=[O:6]

Participants

7

Reactant 3

HCID 11125Lithium CarbonateHCID 660114-Nitrobenzyl bromideHCID 854055-Bromo-3,4-dihydroxybenzaldehyde

Product 1

HCID 86761409HCID 86761409, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-bromo-4,5-dihydroxy-benzaldehyde (2 g), 4-nitrobenzylbromide (2 g), lithium carbonate (680 mg) and a small amount of tetrabutylammonium iodide (ca 50 mg) in DMF (15 ml) was stirred at 60° C. for 4 h. The mixture was diluted with EtOAc and washed with water. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Yield: 2.82 g. MS-ESI: [M+H]+=352.0/354.0

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a601bca44115434e8403382ae38397ef
Source dataset
uspto-grants-2011_09
Patent number
US08017782B2

Reaction notes

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