ChemicalBook CAS DataBase List 4-Chloro-3-(trifluoromethyl)phenyl isocyanate

4-Chloro-3-(trifluoromethyl)phenyl isocyanate synthesis

6synthesis methods

Product Name:4-Chloro-3-(trifluoromethyl)phenyl isocyanate
CAS Number:327-78-6
Molecular formula:C8H3ClF3NO
Molecular Weight:221.56

Phenyl 4-chloro-3-(trifluoromethyl)isocyanate is an important intermediate in the production of the antineoplastic drug sorafenib, which is used in laboratory organic synthesis processes and in pharmaceutical research and development. It can be synthesised in a three-step reaction using 2-Chlorobenzotrifluoride as the starting material.

32315-10-9 Synthesis

32315-10-9
439 suppliers
$10.00/1g

320-51-4 Synthesis

4-Chloro-alpha,alpha,alpha-trifluoro-m-toluidine

320-51-4
476 suppliers
$6.00/10g

4-Chloro-3-(trifluoromethyl)phenyl isocyanate

327-78-6
422 suppliers
$5.00/1g

Yield:327-78-6 100%

Reaction Conditions:

with triethylamine in dichloromethane

Steps:

General procedure C: preparation of N-alkyl-3-oxobenzo[d]isothiazole-2(3H)-carboxamide analogues 6a-w
General procedure: To a solution of triphosgene (2.96 g, 10 mmol) in DCM (20 ml) was added dropwise to primary amine 4 (10 mmol) in DCM (20 ml) followed by the dropwise addition of triethylamine (3 ml) in DCM (10 ml). The solvent was removed on a rotary evaporator. The resulting residue was dissolved in DCM (20 ml), and 1,2-benzisothiazol-3-one (1.51 g, 10 mmol) in THF (20 ml) was added. After the mixture was refluxed for 30 min, the solvent was removed on a rotary evaporator. The residue was dissolved in acetone (30 ml) and mixed with water (30 ml). The precipitate was collected on a funnel by vacuum filtration and washed with water-acetone (1:1,4 × 5 ml) to afford the final compound.

References:

Liu, Dazhi;Tian, Zhen;Yan, Zhihui;Wu, Lixin;Ma, Yan;Wang, Quan;Liu, Wei;Zhou, Honggang;Yang, Cheng [Bioorganic and Medicinal Chemistry,2013,vol. 21,# 11,p. 2960 - 2967]

FullText