2-Bromopropene → HCID 86604774, compound

HRID 1785232Notes

Reaction equation

HRID 1785232 reaction equation
[CH:1]([C:3]1[S:4][C:5]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:6][C:7]=1B(O)O)=[O:2].Br[C:22]([CH3:24])=[CH2:23].[F-].[Cs+]>O1CCOCC1>[C:22]([C:7]1[CH:6]=[C:5]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[S:4][C:3]=1[CH:1]=[O:2])([CH3:24])=[CH2:23]

Participants

5

Reactant 3

HCID 112022-BromopropeneHCID 25953Cesium fluorideHCID 86604775HCID 86604775, compound

Product 1

HCID 86604774HCID 86604774, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 2-Formyl-5-(4-trifluoromethyl-phenyl)-thiophene-3-boronic acid (0.330 g, 1.10 mmole), 2-Bromo-propene (0.399 g, 3.30 mmole) and cesium fluoride (0.585 g, 3.85 mmole) in dioxane (5 mL), is bubbled with nitrogen gas for 15 minutes. The catalyst PdCl2 (dppf) (0.033 g) is then added to the mixture. The reaction is heated under reflux for 16 hours. The solvent is removed on rota vapor, and the resulting residue is partitioned between ethyl acetate (20 ml) and water (20 mL). The aqueous layer is extracted with more ethyl acetate (20 mL). The combined organic solution is washed with brine (3×50 mL), dried over Na2SO4 and concentrated. The crude product is purified on a silica gel column, eluting with 0-15% ethyl acetate in hexane and concentrated to provide the titled compound as pale yellow crystalline.

Workup

  1. customis bubbled with nitrogen gas for 15 minutes
  2. additionThe catalyst PdCl2 (dppf) (0.033 g) is then added to the mixture
  3. temperatureThe reaction is heated
  4. temperatureunder reflux for 16 hours
  5. customThe solvent is removed on rota vapor
  6. customthe resulting residue is partitioned between ethyl acetate (20 ml) and water (20 mL)
  7. extractionThe aqueous layer is extracted with more ethyl acetate (20 mL)
  8. washThe combined organic solution is washed with brine (3×50 mL)
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated
  11. customThe crude product is purified on a silica gel column
  12. washeluting with 0-15% ethyl acetate in hexane
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-15886303a1aa47449c61af5641936167
Source dataset
uspto-grants-2009_03
Patent number
US07504433B2

Reaction notes

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