Thionyl Chloride → 4-(Chloromethyl)-3-(2,6-dichlorophenyl)-5-isopropylisoxazole

HRID 2251319Notes

Reaction equation

HRID 2251319 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14]O)=[C:12]([CH:16]([CH3:18])[CH3:17])[O:11][N:10]=1.S(Cl)([Cl:21])=O>ClCCl>[Cl:21][CH2:14][C:13]1[C:9]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])=[N:10][O:11][C:12]=1[CH:16]([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10850745(3-(2,6-Dichlorophenyl)-5-isopropylisoxazol-4-yl)methanol

Product 1

HCID 592648754-(Chloromethyl)-3-(2,6-dichlorophenyl)-5-isopropylisoxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methanol (15.2 g, 53.1 mmol) in dichloromethane (50 mL) was treated with thionyl chloride (40.0 mL, 54.8 mmol). The reaction was stirred for 1 hour once vigorous bubbling ceased. The solvent and excess reagent were removed in vacuo. Yield=15.96 g. (99%) of 4 (chloromethyl)-3-(2,6-dichlorophenyl)-5-isopropylisoxazole.

Workup

  1. customonce vigorous bubbling
  2. customThe solvent and excess reagent were removed in vacuo

Sources & evidence

ORD record
ord-42fb59fedc03478094824f03d0c1d632
Source dataset
uspto-grants-2008_01
Patent number
US07319109B2

Reaction notes

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