Bromine → HCID 22880250, compound

HRID 565114Notes

Reaction equation

HRID 565114 reaction equation
[CH3:1][C@:2]([OH:17])([CH2:15][CH3:16])[C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)[OH:4].O([Sn](CCCC)(CCCC)CCCC)[Sn](CCCC)(CCCC)CCCC.BrBr>C(Cl)Cl.[F-].[K+].CCOCC>[OH:17][C@@:2]([CH3:1])([CH2:15][CH3:16])[C:3]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:9][CH:10]=1)=[O:4]

Participants

7

Reactant 3

HCID 24408BromineHCID 16682746Bis(tributyltin) oxideHCID 70107279HCID 70107279, compound

Product 1

HCID 22880250HCID 22880250, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 522689Potassium FluorideSolvent

Procedure

To a solution of the crude product from Step 7 (7 g) and (Bu3Sn)2O (30 mL) in 150 mL of CH2Cl2 cooled at 10° C. was added a solution of Br2 (9.3 g in 30 mL of CH2Cl2). After stirring at r.t. for 30 min. the mixture was diluted with a solution of KF (500 mL, 3N) and 500 mL of Et2O. The solid generated was removed by filtration and the filtrate was separated. The organic layer was dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography eluted with 1:1 hexane/EtOAc to give 5 g of the title compound as a yellow oil.

Workup

  1. customThe solid generated was removed by filtration
  2. customthe filtrate was separated
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluted with 1:1 hexane/EtOAc

Sources & evidence

ORD record
ord-5be3a1011a6f4243ac5ef5b604241d76
Source dataset
uspto-grants-2001_01
Patent number
US06169188A

Reaction notes

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