m-Chloroperbenzoic acid → 4-{[t-Butyl(diphenyl)silyl]oxy}-3-fluorophenyl acetate

HRID 1634733Notes

Reaction equation

HRID 1634733 reaction equation
[Si:1]([O:18][C:19]1[CH:24]=[CH:23][C:22](C(=O)C)=[CH:21][C:20]=1[F:28])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=[C:32](C=CC=1)[C:33]([O:35]O)=[O:34]>C(Cl)(Cl)Cl.ClCCl>[C:33]([O:35][C:22]1[CH:23]=[CH:24][C:19]([O:18][Si:1]([C:14]([CH3:16])([CH3:17])[CH3:15])([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[C:20]([F:28])[CH:21]=1)(=[O:34])[CH3:32]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69987244HCID 69987244, compound

Product 1

HCID 699857744-{[t-Butyl(diphenyl)silyl]oxy}-3-fluorophenyl acetate

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

1-(4-{[t-Butyl(diphenyl)silyl]oxy}-3-fluorophenyl)-1-ethanone (8.27 g, 21.07 mmol) was dissolved in chloroform (300 mL). 3-Chloroperoxybenzoic acid (4.0 g, 23.18 mmol) was added and the solution heated to reflux for 72 hours. The solution was diluted with dichloromethane, washed with saturated sodium hydrogen sulfate, saturated sodium hydrogen carbonate, brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent evaporated to dryness in vacuo to yield the title compound which was used without further purification (5.28 g, 12.92 mmol).

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux for 72 hours
  3. washwashed with saturated sodium hydrogen sulfate, saturated sodium hydrogen carbonate, brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe solution was filtered
  6. customthe solvent evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-ef0f1fa36cca49dfa273a12cc80ab30c
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

Loading…