1,2-Dibromoethane → HCID 66997261, compound

HRID 2364949Notes

Reaction equation

HRID 2364949 reaction equation
BrC1C=C[C:5]([NH:9][CH:10]2[CH2:19][CH2:18][C:13]3([O:17][CH2:16][CH2:15][O:14]3)[CH2:12][CH2:11]2)=[C:6]([OH:8])C=1.Br[CH2:21][CH2:22][Br:23].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:23][CH:22]1[CH:10]([CH:11]2[CH:12]=[CH:12][CH2:11][CH2:10][CH2:19]2)[CH2:19][CH2:18][C:13]2([O:14][CH2:15][CH2:16][O:17]2)[CH2:21]1.[O:8]1[CH:6]=[CH:5][N:9]=[CH:10][CH2:19]1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 66726429HCID 66726429, compound

Product 1

HCID 66997261HCID 66997261, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of intermediate D10 (0.433 g, 1.319 mmol), 1,2-dibromoethane (0.341 ml, 3.958 mmol and potassium carbonate (0.912 g, 6.596 mmol) in DMF (10 ml) was heated at 180° C. for 15 min. under microwave irradiation. After cooling to r.t. the r.m. was filtered through diatomaceous earth. The filtrate was evaporated in vacuo. The crude residue was purified by column chromatography (silica gel; DCM as eluent). The desired fractions were collected and evaporated in vacuo to yield a colorless oil that crystallized to yield D12 (0.271 g, 58%).

Workup

  1. temperatureAfter cooling to r.t. the r.m
  2. filtrationwas filtered through diatomaceous earth
  3. customThe filtrate was evaporated in vacuo
  4. customThe crude residue was purified by column chromatography (silica gel; DCM as eluent)
  5. customThe desired fractions were collected
  6. customevaporated in vacuo
  7. customto yield a colorless oil that
  8. customcrystallized

Sources & evidence

ORD record
ord-28679e54c3304542b27d3e780e5b0d0d
Source dataset
uspto-grants-2014_04
Patent number
US08697689B2

Reaction notes

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