Bromine → HCID 67431625, compound

HRID 1040108Notes

Reaction equation

HRID 1040108 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7]1.[Br:16]Br>C(Cl)(Cl)Cl.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>[Br:16][C:5]1[S:1][C:2]([C:6]2([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][CH2:8]2)=[N:3][CH:4]=1

Participants

6

Reactant 2

HCID 24408BromineHCID 67262257HCID 67262257, compound

Product 1

HCID 67431625HCID 67431625, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 24477Sodium ThiosulfateSolventHCID 516892Sodium BicarbonateSolvent2×

Procedure

The product from Step 2 (860 mg, 3.82 mmol) was taken up in CHCl3 (19 mL) and placed in a cool water bath. NaHCO3 (353 mg, 4.20 mmol) was added, followed by bromine (1.22 g, 7.63 mmol). After stirring for 90 min at room temperature, the reaction was diluted with 10% Na2S2O3 and saturated NaHCO3 and extracted with CH2Cl2 (2×). The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated. Flash chromatography (0-10% ether in hexanes) afforded tert-butyl 1-(5-bromo-1,3-thiazol-2-yl)cyclopropanecarboxylate (545 mg, 47%) as a colorless oil. MS ESI: [M-t-Bu]+ m/z 247.9/249.9.

Workup

  1. customplaced in a cool water bath
  2. extractionextracted with CH2Cl2 (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-8c0a643ebb1448f689d4eb19c84f4d9b
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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