Bromine → HCID 69153196, compound

HRID 1744098Notes

Reaction equation

HRID 1744098 reaction equation
[Br:1]Br.[S:3]1[C:7]([N:8]([C:18]([O:20][CH2:21][C:22]([Cl:25])([Cl:24])[Cl:23])=[O:19])[C@H:9]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[CH:6][CH:5]=[N:4]1.C(=O)(O)[O-].[K+]>ClCCl>[Br:1][C:6]1[CH:5]=[N:4][S:3][C:7]=1[N:8]([C:18]([O:20][CH2:21][C:22]([Cl:23])([Cl:24])[Cl:25])=[O:19])[C@H:9]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH:11]([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 24408BromineHCID 516893Potassium BicarbonateHCID 69151351HCID 69151351, compound

Product 1

HCID 69153196HCID 69153196, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromine (85 μL, 1.7 mmol) was added to a solution of methyl N-isothiazol-5-yl-N-[(2,2,2-trichloroethoxy)carbonyl]leucinate (150 mg, 0.370 mmol) in dichloromethane (2.0 mL) over powdered potassium bicarbonate (370 mg, 3.7 mmol) with rapid stirring at rt for 5 h. Excess bromine was quenched by the addition of 1 M aqueous NaHSO3 solution and the mixture was partitioned between water and ether. The layers were separated and the aqueous phase was extracted with additional ether (2×). The extracts were combined, dried (Na2SO4) and concentrated to give 172 mg of methyl N-(4-bromoisothiazol-5-yl)-N-[(2,2,2-trichloroethoxy)carbonyl]leucinate as a yellow oil.

Workup

  1. customExcess bromine was quenched by the addition of 1 M aqueous NaHSO3 solution
  2. customthe mixture was partitioned between water and ether
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with additional ether (2×)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-61a4732089d74cf48b2fcdf5e7f3164f
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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