Carbon Tetrachloride → 5-ChloroMethyl-3-trifluoroMethyl-isoxazole

HRID 1650393Notes

Reaction equation

HRID 1650393 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:7]=[C:6]([CH2:8]O)[O:5][N:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:32]>ClCCl>[Cl:32][CH2:8][C:6]1[O:5][N:4]=[C:3]([C:2]([F:11])([F:10])[F:1])[CH:7]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 133079935-Isoxazolemethanol,3-(trifluoromethyl)-(9CI)

Product 1

HCID 145785335-ChloroMethyl-3-trifluoroMethyl-isoxazoleYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-trifluoromethyl-5-hydroxymethylisoxazole [(700 mg, 4.2 mmol) See K. Tanaka et al, Bull. Chem. Soc. Jpn., 57, 2184 (1984)] and triphenylphosphine (1.43 g, 5.4 mmol) in carbontetrachloride (50 ml) and dichloromethane (20 ml) is heated at reflux for 6 hours. The reaction mixture is then cooled to room temperature and passed through a silica gel plug. Concentration affords in 82% yield the desired 5-chloromethyl-3-trifluoromethylisoxazole of sufficient purity for the following step (Example 24).

Workup

  1. temperatureat reflux for 6 hours
  2. concentrationConcentration

Sources & evidence

ORD record
ord-a9fbc04cf90442eab91d133286653392
Source dataset
uspto-grants-1990_05
Patent number
US04924002

Reaction notes

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