Dichloromethane → HCID 12602096, compound

HRID 1039699Notes

Reaction equation

HRID 1039699 reaction equation
[F:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].C(Cl)Cl.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>O.C(=O)(O)[O-].[Na+].C(OCC)C>[F:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH:3]=[O:4]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 10866415HCID 10866415, compound

Product 1

HCID 12602096HCID 12602096, compoundYield 88.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 516892Sodium BicarbonateSolvent2×

Conditions

Temperature
23 °C

Procedure

To a 500 mL RBF containing 2-fluoro-2-phenylethanol (440.00 mg, 3139 μmol) was added DCM (30 mL) and the mixture was allowed to stir at 23° C. for 5 min. At this time, sodium bicarbonate (343 mg, 4081 μmol) and Dess-MartinPeriodinane (1731 mg, 4081 μmol) were added in one portion and the reaction mixture was allowed to stir for 15 min before the reaction was quenched by the addition of sodium thiosulfate (2482 mg, 15697 μmol) in water (50 ml) and sodium bicarbonate (sat, 50 ml) and diethyl ether (100 ml). The quenched reaction was allowed to stir for 20 min and the organic layer was washed with sodium bicarbonate (sat., 3×75 ml) and brine. The organic layer was dried over magnesium sulphate, filtered and concentrated to give the title compound (385 mg) as a pale yellow oil.

Workup

  1. stirringto stir for 15 min before the reaction
  2. customThe quenched reaction
  3. stirringto stir for 20 min
  4. washthe organic layer was washed with sodium bicarbonate (sat., 3×75 ml) and brine
  5. dry with materialThe organic layer was dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f5435614fe9841128c62a29e1985df3f
Source dataset
uspto-grants-2013_10
Patent number
US08552181B2

Reaction notes

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