Iodine → HCID 66749494, compound

HRID 537037Notes

Reaction equation

HRID 537037 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][CH:11]=[N:10][C:9]=1[C:13]([O:15][CH3:16])=[O:14].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[I:27]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][C:11]([I:27])=[N:10][C:9]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 2733832Lithium HexamethyldisilazideHCID 13290634Methyl 5-(2-chlorophenyl)-1,3-oxazole-4-carboxylate

Product 1

HCID 66749494HCID 66749494, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a round bottom flask were added methyl 5-(2-chlorophenyl)-1,3-oxazole-4-carboxylate (2.25 g, 9.5 mmol) and THF (50 mL). The mixture was cooled to −78° C. LiHMDS (1M in hexane, 12.3 mL, 12.3 mmol) was added dropwise. The mixture was allowed to stir at −78° C. for 1 h. Iodine (3.60 g, 14.2 mmol) was added and the mixture was allowed to stir at −78° C. for 20 min. The mixture was allowed to warm to rt and stir overnight. The reaction mixture was poured into 10% sodium thiosulfate (100 mL) and was extracted with EtOAc. The organic solutions were combined, washed with brine, dried over MgSO4, filtered, and concentrated to give methyl 5-(2-chlorophenyl)-2-iodo-1,3-oxazole-4-carboxylate (3.0 g, 87%) which was used without further purification.

Workup

  1. stirringto stir at −78° C. for 20 min
  2. temperatureto warm to rt
  3. stirringstir overnight
  4. extractionwas extracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-49dbbc1bcc7942c9a3ceadd328f611a5
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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