Dimethyl Sulfoxide → HCID 59157952, compound

HRID 1920519Notes

Reaction equation

HRID 1920519 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.CS(C)=O.C([C:13]1[C:22]2[C:17](=[CH:18][C:19]([CH3:23])=[CH:20][CH:21]=2)[C:16](CC)=[C:15]([CH:26]([P:28](=O)([O-:30])[O-:29])[OH:27])[C:14]=1[Br:32])C.[CH2:33](N(CC)CC)[CH3:34]>C(Cl)Cl.O>[Br:32][C:14]1[C:15]([C:26]([P:28](=[O:29])([O:5][CH2:1][CH3:2])[O:30][CH2:33][CH3:34])=[O:27])=[CH:16][C:17]2[C:22]([CH:13]=1)=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=2

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 131729689HCID 131729689, compound

Product 1

HCID 59157952HCID 59157952, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (0.15 mL) in 2.5 mL of CH2Cl2 at −78° C. was added DMSO (0.23 mL). The reaction was stirred for 10 minutes after which a solution of diethyl(3-bromo-7-methyl-2-naphthyl)(hydroxy)methylphosphonate (160 mg), in 2.5 mL CH2Cl2 was added dropwise. The reaction was stirred for 1 h at −78° C. after which triethylamine (0.66 mL) was added to the mixture and the temperature was raised to rt. Water (5 mL) was added and the mixture was extracted with CH2Cl2. The organic extracts were combined, dried over Na2SO4 and evaporated to dryness to afford the titled product which was used as such in the next step.

Workup

  1. additionwas added to the mixture
  2. extractionthe mixture was extracted with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-77f213e608e944fea6aa7ecafb7e71bf
Source dataset
uspto-grants-2012_05
Patent number
US08168815B2

Reaction notes

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