Thionyl Chloride → 4-(3-(4-(Trifluoromethoxy)phenoxy)azetidin-1-yl) butyryl chloride

HRID 1043534Notes

Reaction equation

HRID 1043534 reaction equation
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:20]=[CH:19][C:7]([O:8][CH:9]2[CH2:12][N:11]([CH2:13][CH2:14][CH2:15][C:16](O)=[O:17])[CH2:10]2)=[CH:6][CH:5]=1.S(Cl)([Cl:25])=O>>[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:20]=[CH:19][C:7]([O:8][CH:9]2[CH2:12][N:11]([CH2:13][CH2:14][CH2:15][C:16]([Cl:25])=[O:17])[CH2:10]2)=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 866859084-(3-(4-(Trifluoromethoxy)phenoxy)azetidin-1-yl)butyric acid

Product 1

HCID 866859074-(3-(4-(Trifluoromethoxy)phenoxy)azetidin-1-yl) butyryl chlorideYield 97%

Procedure

4-(3-(4-(trifluoromethoxy)phenoxy)azetidin-1-yl)butyric acid (412 mg, 1.29 mmol) was dissolved in thionyl chloride, raised the temperature to reflux for 3 h, spun dry, residuals were washed by an appropriate amount of ethyl ether, generated 421 mg target product, yield was 97%, directly put to the next reaction step.

Workup

  1. temperatureraised the temperature
  2. temperatureto reflux for 3 h
  3. customspun dry
  4. washresiduals were washed by an appropriate amount of ethyl ether
  5. customdirectly put to the next reaction step

Sources & evidence

ORD record
ord-8b5babe20b4d44be88950e1bfc52c71c
Source dataset
uspto-grants-2013_10
Patent number
US08563547B2

Reaction notes

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