Thionyl Chloride → 2-(3-(Chloromethyl)-5-ethoxyphenoxy)-5-(trifluoromethyl)pyridine

HRID 1666438Notes

Reaction equation

HRID 1666438 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:21]O)[CH:7]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]=2)[CH:9]=1)[CH3:2].S(Cl)([Cl:25])=O>ClCCl>[Cl:25][CH2:21][C:6]1[CH:7]=[C:8]([CH:9]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1)[O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66876312(3-Ethoxy-5-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methanol

Product 1

HCID 668756612-(3-(Chloromethyl)-5-ethoxyphenoxy)-5-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3-Ethoxy-5-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methanol from Step 2 (350 mg, 1.12 mmol), in dichloromethane (3 mL), was cooled to 0° C., and treated dropwise with thionyl chloride (0.122 mL, 1.68 mmol). The reaction mixture was allowed to warm to ambient temperature and was stirred for 3 h. The mixture was evaporated in vacuo to afford the desired product as an oil.

Workup

  1. customThe mixture was evaporated in vacuo

Sources & evidence

ORD record
ord-93a8637e338f41ae968378ed3660ec92
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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