Carbon Tetrachloride → 3-(Chloromethyl)-5-[3,5-bis(trifluoromethyl)phenyl]isoxazole

HRID 913719Notes

Reaction equation

HRID 913719 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([CH2:18]O)[CH:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:42]>>[Cl:42][CH2:18][C:15]1[CH:14]=[C:13]([C:5]2[CH:4]=[C:3]([C:2]([F:21])([F:20])[F:1])[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=2)[O:17][N:16]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 57800356{5-[3,5-bis(Trifluoromethyl)phenyl]-3-isoxazolyl}methanol

Product 1

HCID 578002023-(Chloromethyl)-5-[3,5-bis(trifluoromethyl)phenyl]isoxazole

Conditions

Temperature
75 °C

Procedure

To a solution of {5-[3,5-bis(trifluoromethyl)phenyl]-3-isoxazolyl}methanol (Example 323B) (0.100 g, 0.32 mmol) in dry carbon tetrachloride (15 mL) was added PS-triphenylphosphine (0.292 g, 2.2 mmol/g, 0.64 mmol). The reaction was heated at 75° C. overnight. The resin was filtered and washed with carbon tetrachloride. Concentration in vacuo afforded the title compound, which was used for the next step without further purification.

Workup

  1. filtrationThe resin was filtered
  2. washwashed with carbon tetrachloride
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-8c6be984def744688351197368656db8
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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