Dimethyl Sulfoxide → HCID 86613082, compound

HRID 1869142Notes

Reaction equation

HRID 1869142 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Cl:11][C:12]1[CH:33]=[C:32]([O:34][CH2:35][CH:36]=[C:37]([Cl:39])[Cl:38])[CH:31]=[C:30]([Cl:40])[C:13]=1[O:14][CH2:15][CH:16]([OH:29])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1.C(N(CC)CC)C>ClCCl.O>[Cl:11][C:12]1[CH:33]=[C:32]([O:34][CH2:35][CH:36]=[C:37]([Cl:38])[Cl:39])[CH:31]=[C:30]([Cl:40])[C:13]=1[O:14][CH2:15][C:16](=[O:29])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86613081HCID 86613081, compound

Product 1

HCID 86613082HCID 86613082, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

1.15 ml of dimethyl sulfoxide are added at −60° C. in the course of 5 minutes to 0.63 ml of oxalyl chloride in 50 ml of dichloromethane. After 40 minutes, a solution of 3.4 g of 1-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-3-(4-trifluoromethyl-phenoxy)-propan-2-ol in 30 ml of dichloromethane is added dropwise in the course of 10 minutes. After 40 minutes, 4.5 ml of triethylamine are added and the reaction mixture is slowly heated to room temperature. The reaction mixture is then poured into water and extracted with dichloromethane. After concentration of the organic phase and crystallisation from diethyl ether/hexane, 1-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-3-(4-trifluoromethyl-phenoxy)-propan-2-one is obtained. 1H-NMR (CDCl3) 300 MHz: 4.61 (d, 2H), 4.74 (s, 2H), 5.21 (s, 2H), 6.12 (t, 1H), 6.90 (s, 2H), 7.11 (d, 2H), 7.59 (d, 2H)

Workup

  1. waitAfter 40 minutes
  2. extractionextracted with dichloromethane
  3. customAfter concentration of the organic phase and crystallisation from diethyl ether/hexane

Sources & evidence

ORD record
ord-442f9b5429fc411da1fb88fd74b5be14
Source dataset
uspto-grants-2009_12
Patent number
US07638514B2

Reaction notes

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