Ethyl Acetate → HCID 69829959, compound

HRID 1386945Notes

Reaction equation

HRID 1386945 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11]C(O)=O)=[C:6]([F:15])[CH:5]=1.[Xe](F)[F:18].CCOC(C)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][F:18])=[C:6]([F:15])[CH:5]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 83674Xenon difluorideHCID 69829296HCID 69829296, compound

Product 1

HCID 69829959HCID 69829959, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-carboxymethoxy-3-fluoro-benzoic acid methyl ester (2.73 g, 11.9 mmol) in CH2Cl2 was treated with xenon difluoride (2.23 g 13.1 mmol, 1.1 eq.) at r.t. for 16 hrs. in a teflon reactor vessel. After addition of satd. NaHCO3 solution the organic phase was dried over Na2SO4 and evaporated. The residue was chromatographed over 100 g SiO2 (Merck 230-400 mesh) with EtOAc/nHexane 1:4 affording the title compound (1.24 g, 51% yield) as a white solid. MS: m/e=202 (M+).

Workup

  1. additionAfter addition of satd
  2. dry with materialNaHCO3 solution the organic phase was dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-e53d34f519dd458bb7f15311ade554e6
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

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