Thionyl Chloride → 3-(Chloromethyl)-5-(4-(trifluoromethyl)phenyl)-4,5-dihydroisoxazole

HRID 1795027Notes

Reaction equation

HRID 1795027 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:13][N:12]=[C:11]([CH2:14]O)[CH2:10]2)=[CH:5][CH:4]=1.S(Cl)([Cl:20])=O>C(Cl)Cl>[Cl:20][CH2:14][C:11]1[CH2:10][CH:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:17])([F:16])[F:1])=[CH:4][CH:5]=2)[O:13][N:12]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22184760(5-(4-(Trifluoromethyl)phenyl)-4,5-dihydroisoxazol-3-yl)methanol

Product 1

HCID 221846993-(Chloromethyl)-5-(4-(trifluoromethyl)phenyl)-4,5-dihydroisoxazoleYield 21.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of (5-(4-(trifluoromethyl)phenyl)-4,5-dihydroisoxazol-3-yl)methanol (245 mg, 1.0 mmol) in methylene chloride (15 mL) was added thionyl chloride (200 μL, 2.74 mmol) dropwise at 0° C. The resulting mixture was stirred under an atmosphere of nitrogen for 15 hours, concentrated under reduced pressure, and purified by preparative chromatography (3:7 EtOAc:hexane) to yield 3-(chloromethyl)-5-(4-(trifluoromethyl)phenyl)-4,5-dihydroisoxazole (56 mg, M+1=264.1).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by preparative chromatography (3:7 EtOAc:hexane)

Sources & evidence

ORD record
ord-2c42ca1033a740739790d230710213e2
Source dataset
uspto-grants-2006_04
Patent number
US07026321B2

Reaction notes

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