1,2-Dibromoethane → HCID 67050664, compound

HRID 1498090Notes

Reaction equation

HRID 1498090 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]1[NH:13][CH:14]=[CH:15][N:16]=1)[C:5]([O:7][CH3:8])=[O:6].Br[CH2:18][CH2:19]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[N:16]1[CH:15]=[CH:14][N:13]2[C:12]=1[C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[O:1][CH2:19][CH2:18]2

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 10796Cesium carbonateHCID 135742048HCID 135742048, compound

Product 1

HCID 67050664HCID 67050664, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of methyl 3-hydroxy-4-(1H-imidazol-2-yl)benzoate (2.2 g, 10 mmol), 1,2-dibromoethane (3.12 mL, 36 mmol) and cesium carbonate (13.14 g, 40 mmol) in DMF (100 mL) was heated at 90° C. for 12 hours. The mixture was filtered, the mother liquor was concentrated in vacuo, and the residue was partitioned between water and ethyl acetate. The suspension was filtered and the solid was pure byproduct. The organic layer was washed with water, brine and dried over MgSO4 and concentrated to give crude methyl 5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxylate (2 g, 80%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe mother liquor was concentrated in vacuo
  3. customthe residue was partitioned between water and ethyl acetate
  4. filtrationThe suspension was filtered
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-351300fcbbd142e4a640946c9edfb19e
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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