Cyanuric chloride → 3-[3-Chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]cyclobutanol

HRID 1499828Notes

Reaction equation

HRID 1499828 reaction equation
[Cl:1][C:2]1[C:3]([CH3:18])=[C:4]([CH:13]2[CH2:16][CH:15]([OH:17])[CH2:14]2)[C:5]([O:11][CH3:12])=[C:6]([CH:8](O)[CH3:9])[CH:7]=1.N1C(Cl)=NC(Cl)=NC=1[Cl:21]>CS(C)=O.CCOCC.O>[Cl:1][C:2]1[C:3]([CH3:18])=[C:4]([CH:13]2[CH2:16][CH:15]([OH:17])[CH2:14]2)[C:5]([O:11][CH3:12])=[C:6]([CH:8]([Cl:21])[CH3:9])[CH:7]=1

Participants

6

Reactant 2

HCID 7954Cyanuric chlorideHCID 866777523-[3-Chloro-5-(1-hydroxyethyl)-6-methoxy-2-methylphenyl]cyclobutanol

Product 1

HCID 866777513-[3-Chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]cyclobutanolYield 40.3%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-[3-chloro-5-(1-hydroxyethyl)-6-methoxy-2-methylphenyl]cyclobutanol (170 mg, 0.628 mmol) in dimethyl sulfoxide (1 mL) was added cyanuric chloride (64 mg, 0.34 mmol). After stirred overnight, the reaction mixture was diluted with ether and water. The aqueous layer was extracted with ethyl acetate once. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The crude was purified with silica gel column to give the desired product (39.6 mg, 22%). LCMS calculated for C14H18ClO2(M−Cl)+: m/z=253.1; Found: 253.2.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate once
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was purified with silica gel column

Sources & evidence

ORD record
ord-82093d9be358456da73e43e47b49e067
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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