1,2-Dibromoethane → HCID 86693046, compound

HRID 575011Notes

Reaction equation

HRID 575011 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[C:4]([C:10]2[NH:11][CH:12]=[CH:13][N:14]=2)[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:22][CH2:23]Br>CN(C)C=O>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]2[O:9][CH2:23][CH2:22][N:11]3[C:10](=[N:14][CH:13]=[CH:12]3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 78391,2-Dibromoethane2×HCID 10796Cesium carbonateHCID 136336830HCID 136336830, compound

Product 1

HCID 86693046HCID 86693046, compoundYield 224.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Into a 20-L 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of 4-bromo-5-fluoro-2-(1H-imidazol-2-yl)phenol (755 g, 2.94 mol, 1.00 equiv) in N,N-dimethylformamide (7.5 L), Cs2CO3 (3350 g, 10.28 mol, 3.50 equiv), followed by the addition of 1,2-dibromoethane (2208 g, 11.75 mol, 4.00 equiv). The resulting solution was stirred overnight at 80° C. To this was added 1,2-dibromoethane (200 g). The resulting solution was stirred at 80° C. for 5.5 h. This reaction was repeated for 2 times. The reaction mixture was cooled to room temperature and diluted with 20 L of ice/water. The solids were collected by filtration, washed with 2×4 L of water and dried to afford 1870 g (crude) of 9-Bromo-8-fluoro-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene as a gray solid.

Workup

  1. customInto a 20-L 4-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringThe resulting solution was stirred at 80° C. for 5.5 h
  4. temperatureThe reaction mixture was cooled to room temperature
  5. filtrationThe solids were collected by filtration
  6. washwashed with 2×4 L of water
  7. customdried

Sources & evidence

ORD record
ord-7431ed1ca0e34c07a97e3c134d8efeba
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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