7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-one → 7-bromo-4-fluoro-2-methoxy-9-vinyl-9H-xanthen-9-ol

HRID 335977Notes

Reaction equation

HRID 335977 reaction equation
[CH:1]([Mg]Cl)=[CH2:2].[Br:5][C:6]1[CH:19]=[C:18]2[C:9]([O:10][C:11]3[C:12]([F:23])=[CH:13][C:14]([O:21][CH3:22])=[CH:15][C:16]=3[C:17]2=[O:20])=[CH:8][CH:7]=1>C1COCC1>[Br:5][C:6]1[CH:19]=[C:18]2[C:9]([O:10][C:11]3[C:12]([F:23])=[CH:13][C:14]([O:21][CH3:22])=[CH:15][C:16]=3[C:17]2([CH:1]=[CH2:2])[OH:20])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 574756397-bromo-4-fluoro-2-methoxy-9H-xanthen-9-oneHCID 178461836HCID 178461836, compound

Product 1

HCID 673829547-bromo-4-fluoro-2-methoxy-9-vinyl-9H-xanthen-9-olYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of vinylmagnesium chloride (55.9 ml, 89.4 mmol) at −78° C. was added dropwise of a solution of 7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-one (8.0 g, 24.76 mmol) in THF (99 mL). After 30 min, the reaction was allowed to slowly warm to rt, then quenched with 240 mL of saturated aqueous NH4Cl. The mixture was extracted with EtOAc. The organic layer was dried over magnesium sulfate, filtered and concentrated to yield 7-bromo-4-fluoro-2-methoxy-9-vinyl-9H-xanthen-9-ol (8.69 g, 24.76 mmol, 100% yield) as yellow solid.

Workup

  1. customquenched with 240 mL of saturated aqueous NH4Cl
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ec8c51948787402e9949e5f80debe846
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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