Dimethylformamide → HCID 86681772, compound

HRID 1019625Notes

Reaction equation

HRID 1019625 reaction equation
C1N2CCN(CC2)C1.[Br:9][C:10]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=1[CH:12]=[O:13].CN(C=O)C.[C:24]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])(=[O:27])[CH:25]=[CH2:26]>O>[Br:9][C:10]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=1[CH:12]([OH:13])[C:25](=[CH2:26])[C:24]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9237Dabco2×HCID 15458tert-Butyl acrylateHCID 27733212-Bromo-5-fluorobenzaldehyde

Product 1

HCID 86681772HCID 86681772, compoundYield 114.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Alternate Preparation. This procedure uses DABCO as a more economical substitute for (4s)-quinuclidin-3-ol. A 1 L flask was charged with 2-bromo-5-fluorobenzaldehyde (13.4 g, 66.0 mmol), DABCO (14.81 g, 132 mmol), DMF (53.6 mL) and water (13.4 mL). To this reaction mixture was added tert-butyl acrylate (12.68 g, 99.0 mmol). The mixture was then stirred at rt for 12 h. At this time TLC indicated consumption of starting material. The reaction mixture was diluted with 25 mL of water and then extracted with two 100 mL portions of MTBE. The combined organic phases were washed with 0.1N HCl, water and brine. It was then dried over MgSO4, filtered and concentrated to yield 25 g (>100%) of the product as a colorless oil which was used without further purification.

Workup

  1. customAlternate Preparation
  2. customconsumption of starting material
  3. additionThe reaction mixture was diluted with 25 mL of water
  4. extractionextracted with two 100 mL portions of MTBE
  5. washThe combined organic phases were washed with 0.1N HCl, water and brine
  6. dry with materialIt was then dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bff9f58d12a94190ac69923356b6fd2a
Source dataset
uspto-grants-2014_05
Patent number
US08716275B2

Reaction notes

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