Potassium Carbonate → HCID 67187347, compound

HRID 1186039Notes

Reaction equation

HRID 1186039 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:5](=[CH:10][C:11]([CH2:16]Br)=[C:12]([CH2:14]Br)[CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].[OH:19][C:20]1[CH:21]=[C:22]([C:29]#[N:30])[C:23](=[CH:26][C:27]=1[OH:28])[C:24]#[N:25].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:1][O:2][C:3]([C:4]1[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][C:11]2[CH2:16][O:19][C:20]3[CH:21]=[C:22]([C:29]#[N:30])[C:23]([C:24]#[N:25])=[CH:26][C:27]=3[O:28][CH2:14][C:12]=2[CH:13]=1)=[O:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6433904,5-dihydroxyphthalonitrileHCID 67187642Dimethyl 4,5-bis(bromomethyl)benzene-1,2-dicarboxylate

Product 1

HCID 67187347HCID 67187347, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A slurry of 4,5-bis-bromomethyl-phthalic acid dimethyl ester (1.57 g, 4.12 mmol), 4,5-dihydroxy-phthalonitrile (660 mg, 4.12 mmol) and potassium carbonate (1.1 g, 8.24 mmol) in DMF (20 mL) was heated to 60° C. for 1 h under an atmosphere of argon. The resulting slurry was cooled to room temperature and diluted with water. A white precipitate was collected via filtration and re-crystallized from EtOAc to yield 2,3-dicyano-6,11-dihydro-5,12-dioxa-dibenzo[a,e]cyclooctene-8,9-dicarboxylic acid dimethyl ester as a white solid. C20H14N2O6; MS (ESI) m/z 378.9 (MH)+.

Workup

  1. filtrationA white precipitate was collected via filtration
  2. customre-crystallized from EtOAc

Sources & evidence

ORD record
ord-9021c6b0e2c241de88e9e11cfa85d1b5
Source dataset
uspto-grants-2014_03
Patent number
US08673890B2

Reaction notes

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