Water → 4-Chloro-2-(3-chloromethyl-2-methysulfanyl-phenoxy)-benzonitrile

HRID 1243759

Reaction equation

[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17]N(C)C)[C:12]=2[S:21][CH3:22])[CH:3]=1.C1(C)C=CC=CC=1.[Cl:30]C(OCC)=O.O>C(OCC)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][Cl:30])[C:12]=2[S:21][CH3:22])[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Under a nitrogen atmosphere, 4-chloro-2-(3-dimethylaminomethyl-2-methysulfanyl-phenoxy)-benzonitrile (1.02 g, 3.06 mmol) was dissolved in anhydrous-toluene (10 mL). The solution was cooled to 0° C. and ethyl chloroformate (900 μL, 9.2 mmol) was slowly added. The reaction mixture was stirred for 17 h, allowing it to reach room temperature. Water (5 mL) and diethyl ether (5 mL) were added and the organic layer was separated and dried with MgSO4. After filtration, the solution was absorbed onto silica gel (1.5 g) and the solvent was removed in vacuo. This material was chromatographed on an ISCO CombiFlash Chromatography System to yield 4-chloro-2-(3-chloromethyl-2-methysulfanyl-phenoxy)-benzonitrile as a clear oil (800 mg, 81%).

Workup

customto reach room temperature
customthe organic layer was separated
dry with materialdried with MgSO4
filtrationAfter filtration
customthe solution was absorbed onto silica gel (1.5 g)
customthe solvent was removed in vacuo
customThis material was chromatographed on an ISCO CombiFlash Chromatography System

Sources & evidence

ORD record: ord-3c3f81cd38d54960bb8e4b247aa2546b
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119122B2

Linked notes

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