HCID 57475644, compound → HCID 57475651, compound

HRID 931566Notes

Reaction equation

HRID 931566 reaction equation
[CH:1]([Mg]Cl)=[CH2:2].[Br:5][C:6]1[CH:19]=[CH:18][C:17]2[O:16][C:15]3[C:10](=[CH:11][C:12]([I:20])=[CH:13][CH:14]=3)[C:9](=[O:21])[C:8]=2[CH:7]=1>C1COCC1>[Br:5][C:6]1[CH:19]=[CH:18][C:17]2[O:16][C:15]3[C:10](=[CH:11][C:12]([I:20])=[CH:13][CH:14]=3)[C:9]([CH:1]=[CH2:2])([OH:21])[C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 57475644HCID 57475644, compoundHCID 178461836HCID 178461836, compound

Product 1

HCID 57475651HCID 57475651, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of vinylmagnesium chloride (6.86 mL, 10.97 mmol) at −78° C. under nitrogen atmosphere was added drop wise a solution of 2-bromo-7-iodo-9H-xanthen-9-one (2.00 g, 4.99 mmol) in THF (30 mL). The reaction mixture was allowed to slowly warm to −10° C., then the reaction was quenched with saturated NH4Cl. The mixture was extracted with EtOAc followed by a solvent mixture of CHCl3:i-PrOH (3:1). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by filtration over silica gel (10% EtOAc/hexane) to give 2.14 g of 2-bromo-7-iodo-9-vinyl-9H-xanthen-9-ol as a white solid.

Workup

  1. customthe reaction was quenched with saturated NH4Cl
  2. extractionThe mixture was extracted with EtOAc
  3. additionfollowed by a solvent mixture of CHCl3:i-PrOH (3:1)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. filtrationThe crude material was purified by filtration over silica gel (10% EtOAc/hexane)

Sources & evidence

ORD record
ord-e5e2800679b34caab80fefa0756cf872
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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