Bromine → HCID 13914095, compound

HRID 1709708Notes

Reaction equation

HRID 1709708 reaction equation
[CH:1]([S:4][C:5]1[S:6][CH:7]=[C:8]([O:10][S:11]([CH3:14])(=[O:13])=[O:12])[N:9]=1)([CH3:3])[CH3:2].[Br:15]Br.S([O-])(O)=O.[Na+]>CCOCC>[CH:1]([S:4][C:5]1[S:6][C:7]([Br:15])=[C:8]([O:10][S:11]([CH3:14])(=[O:12])=[O:13])[N:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24408BromineHCID 13914034HCID 13914034, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 13914095HCID 13914095, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3.5 g of 2-isopropylthio-4-methylsulfonyloxy-1,3-thiazole was dissolved in 50 ml of ether, and 0.8 ml of bromine was added dropwise to the solution keeping the temperature below 0° C. After the addition, the solution was stirred at room temperature for 2 hours, then 5% solution of sodium hydrogen sulfite was added thereto to separate ether layer, which was washed with water and dried over anhydrous sodium sulfate, followed by concentration to an oil. The oil was purified by silica-gel column chromatography to obtain 3.7 g of the objective compound as a yellow oil (yield: 80.7%).

Workup

  1. customthe temperature below 0° C
  2. additionAfter the addition
  3. customto separate ether layer, which
  4. washwas washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationfollowed by concentration to an oil
  7. customThe oil was purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-dc45cb58954945c4a5a90b90142b173e
Source dataset
uspto-grants-1990_08
Patent number
US04950679

Reaction notes

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