2,2-Difluoroethyl trifluoromethanesulfonate → 2-Chloro-5-(2,2-difluoroethoxy)-4-methylpyridine

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.FC(F)(F)S(O[CH2:16][CH:17]([F:19])[F:18])(=O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([O:8][CH2:16][CH:17]([F:19])[F:18])=[CH:6][N:7]=1

Participants

Reactant 2

HCID 27740892,2-Difluoroethyl trifluoromethanesulfonate

HCID 712995492-Chloro-5-hydroxy-4-methylpyridine

Product 1

HCID 898755182-Chloro-5-(2,2-difluoroethoxy)-4-methylpyridineYield 95%

Procedure

The title compound is prepared in 95% yield (4.14 g, white solid) from 6-chloro-4-methylpyridin-3-ol (3.0 g, 20.9 mmol) and 2,2-difluoroethyl trifluoromethanesulfonate (4.92 g, 23.0 mmol) in a similar manner to Step-1 of Amine-49.

Sources & evidence

ORD record: ord-eaabdeb5e15f420f88e027d2dd668752
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187475B2

Reaction notes

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