(8-bromo-6-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate → (8-bromo-6-fluoro-3,4-dihydro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate

HRID 902311Notes

Reaction equation

HRID 902311 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]2[CH:22]=[CH:21][C:20]3[C:15](=[C:16]([Br:24])[CH:17]=[C:18]([F:23])[CH:19]=3)[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H][H]>C(O)C.[Pt]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][CH:13]2[CH2:22][CH2:21][C:20]3[C:15](=[C:16]([Br:24])[CH:17]=[C:18]([F:23])[CH:19]=3)[O:14]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 86609107(8-bromo-6-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonateHCID 178418361HCID 178418361, compound

Product 1

HCID 86609108(8-bromo-6-fluoro-3,4-dihydro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonateYield 49%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A solution of (8-bromo-6-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate (300 mg, 0.73 mmol) in absolute ethanol was added to 5% sulfided platinum on carbon (50 mg) and the mixture hydrogenated at 55 psi of hydrogen for 1 hour. The mixture was then filtered through celite and the filtrate concentrated under reduced pressure to afford a white semi-solid. Purification by flash chromatography using a solvent gradient of 5 to 25% ethyl acetate in hexane gave 148 mg (49%) of (8-bromo-6-fluoro-3,4-dihydro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate as a white solid.

Workup

  1. filtrationThe mixture was then filtered through celite
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customto afford a white semi-solid
  4. customPurification by flash chromatography

Sources & evidence

ORD record
ord-d5e2d53eb25f4f108630de28700b71e8
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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