1,2-Dibromoethane → HCID 67050664, compound

HRID 2044251Notes

Reaction equation

HRID 2044251 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-a50759a2e14242b18e5cb66cb12c04e6
Source dataset
uspto-grants-2013_11
Patent number
US08586574B2

Reaction notes

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