HCID 86609106, compound → (8-bromo-6-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate

HRID 902310Notes

Reaction equation

HRID 902310 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]([O:16][C:17]2[C:22](/[CH:23]=C/C)=[CH:21][C:20]([F:26])=[CH:19][C:18]=2[Br:27])[CH:14]=C)(=[O:10])=[O:9])=[CH:4][CH:3]=1>ClCCl.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1C=CC(C=[Ru](Cl)Cl)=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][CH:13]2[CH:14]=[CH:23][C:22]3[C:17](=[C:18]([Br:27])[CH:19]=[C:20]([F:26])[CH:21]=3)[O:16]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86609106HCID 86609106, compound

Product 1

HCID 86609107(8-bromo-6-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonateYield 96%

Reagents, catalysts & solvents 2

HCID 11967259Benzylidenebis(tricyclohexylphosphine)dichlororutheniumCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-{2-bromo-4-fluoro-6-[(1E)-prop-1-enyl]phenoxy}but-3-enyl 4-methylbenzenesulfonate (10.95 g, 0.024 mol) in dry dichloromethane (300 mL) at room temperature under nitrogen was added benzylidene-bis(tricyclohexylphosphine)dichlororuthenium (1.97 g, 2.4 mmol) and the reaction mixture stirred at room temperature for 5 days. The reaction mixture was then concentrated under reduced pressure to a small volume and directly pre-adsorbed onto silica gel. Purification by flash chromatography using a solvent gradient of 5 to 30% ethyl acetate in hexane gave 9.5 g (96%) of (8-bromo-6-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate as a grey solid.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure to a small volume and directly pre-adsorbed onto silica gel
  2. customPurification by flash chromatography

Sources & evidence

ORD record
ord-c16dcca0368340cfb89b9bec1318ad43
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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