Ethyl iodoacetate → [2-(2-Chloro-6-fluoro-phenyl)-ethoxy]-acetic acid ethyl ester

HRID 2100533Notes

Reaction equation

HRID 2100533 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][CH2:10][OH:11].I[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(C1C=CC=C(C(C)(C)C)N=1)(C)(C)C>FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][O:11][CH2:10][CH2:9][C:3]1[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[CH3:18]

Participants

5

Reactant 3

HCID 12183Ethyl iodoacetateHCID 685102,6-Di-tert-butylpyridineHCID 27332352-(2-Chloro-6-fluorophenyl)ethanol

Product 1

HCID 68564810[2-(2-Chloro-6-fluoro-phenyl)-ethoxy]-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 76223Silver(I) trifluoromethanesulfonateCatalyst

Procedure

In analogy to the procedure described in example 78.1, 2-(2-chloro-6-fluoro-phenyl)-ethanol was reacted with ethyl iodoacetate in the presence of silver trifluoromethanesulfonate and 2,6-di-tert-butylpyridin to give [2-(2-chloro-6-fluoro-phenyl)-ethoxy]-acetic acid ethyl ester as colorless liquid. 1H NMR (CDCl3): 1.28 (t, J=7.1 Hz, 3H), 3.15 (t, J=7.1 Hz, 2H), 3.73 (t, J=7.3 Hz, 2H), 4.11 (s, 2H), 4.22 (q, J=7.1 Hz, 2H), 6.96 (m, 1H), 7.09-7.19 (m, 2H).

Sources & evidence

ORD record
ord-52554209fc5a4679b5c26c45f7c589c9
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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