Dichloromethane → 1-(3-(tert-Butyldimethylsilyloxy)-2,5-difluorophenyl)propan-1-one

HRID 1662563Notes

Reaction equation

HRID 1662563 reaction equation
[Si:1]([O:8][C:9]1[C:10]([F:20])=[C:11]([CH:16]([OH:19])[CH2:17][CH3:18])[CH:12]=[C:13]([F:15])[CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(Cl)Cl.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>CCOC(C)=O.CC1(C)N([O])C(C)(C)CCC1>[Si:1]([O:8][C:9]1[C:10]([F:20])=[C:11]([C:16](=[O:19])[CH2:17][CH3:18])[CH:12]=[C:13]([F:15])[CH:14]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 12217721Iodo benzene diacetateHCID 577069101-(3-(tert-Butyldimethylsilyloxy)-2,5-difluorophenyl)propan-1-ol

Product 1

HCID 577063781-(3-(tert-Butyldimethylsilyloxy)-2,5-difluorophenyl)propan-1-oneYield 94%

Reagents, catalysts & solvents 2

HCID 2724126TempoCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 200 mL round bottom flask was charged with 90.C (0.48 g, 1.6 mmol), DCM (15 mL), iodobenzene diacetate (0.56 g, 1.7 mmol), and TEMPO (0.012 g, 0.079 mmol). The mixture was stirred overnight at room temperature and diluted with EtOAc. The organics were washed with saturated aqueous sodium thiosulfate, saturated aqueous sodium bicarbonate, and brine, dried (MgSO4), and concentrated. The crude product was purified by silica gel flash chromatography (0-5% EtOAc/hexane) to afford 90.D (0.45 g, 94% yield) as a colorless oil.

Workup

  1. washThe organics were washed with saturated aqueous sodium thiosulfate, saturated aqueous sodium bicarbonate, and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel flash chromatography (0-5% EtOAc/hexane)

Sources & evidence

ORD record
ord-f33779ab823d447c906d34157bd2ab42
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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