Methyl alpha-phenylbenzeneacetate → Methyl 2-fluoro-2,2-diphenylacetate

HRID 2260846Notes

Reaction equation

HRID 2260846 reaction equation
[CH:1]([C:14]([O:16][CH3:17])=[O: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.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:28])(=O)=O)=CC=1>O1CCCC1>[C:1]([C:14]([O:16][CH3:17])=[O:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[F:28]

Participants

4

Reactant 2

HCID 77019Methyl alpha-phenylbenzeneacetateHCID 588007N-Fluorobenzenesulfonimide

Product 1

HCID 13222568Methyl 2-fluoro-2,2-diphenylacetateYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4.8 milliliters KN(SiCH3)2 were dropped into 5 milliliters (C6H5)2CHCOOCH3 in tetrahydrofuran at -78° C. and the resulting yellow suspension was stirred for 45 minutes. 1.2 molar equivalents N-fluorobenzenesulfonimide prepared according to Example 1 above in 4 milliliters tetrahydrofuran were dropped into the mixture and stirring continued at -78° C. for 1 hour. The mixture was allowed to warm up to room temperature, quenched with ammonium chloride, and acidified with 0.1N hydrogen chloride. Extraction with dichloromethane, drying, and evaporation were followed by purification on a silica gel column. White crystalline (C6H5)2CFCOOCH3 was obtained in 82% yield.

Workup

  1. additionwere dropped into the mixture
  2. stirringstirring
  3. waitcontinued at -78° C. for 1 hour
  4. customquenched with ammonium chloride
  5. extractionExtraction with dichloromethane
  6. customdrying
  7. customevaporation
  8. customwere followed by purification on a silica gel column

Sources & evidence

ORD record
ord-20563301f2034ea28d4c13ef858f2b9f
Source dataset
uspto-grants-1995_12
Patent number
US05478964

Reaction notes

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