3-Bromo-3-methyl-2-butanone → 2-Methyl-3-oxobutan-2-yl thiocyanate

HRID 127233Notes

Reaction equation

HRID 127233 reaction equation
Br[C:2]([CH3:7])([CH3:6])[C:3](=[O:5])[CH3:4].[C:8]([S-:10])#[N:9].[K+]>CC(C)=O>[CH3:6][C:2]([S:10][C:8]#[N:9])([CH3:7])[C:3](=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 3449113-Bromo-3-methyl-2-butanoneHCID 516872Potassium thiocyanate

Product 1

HCID 141951652-Methyl-3-oxobutan-2-yl thiocyanate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

16.5 g. (0.1 mol) of 3-bromo-3-methyl-2-butanone and 11.6 g. (0.12 mol) of potassium rhodanide were refluxed for 1-2 hours in 150 ml. of anhydrous acetone. After cooling, the separated potassium bromide was filtered under suction, back-washed with a small amount of acetone and evaporated to dryness in vacuo at 50° C. The residue was taken up in 200 ml. of ether and washed three times with 100 ml. of water. The ether phase was dried over sodium sulfate and evaporated to dryness in vacuo. The crude product was fractionated on a short Vigreux column to yield 3-methyl-3-thiocyanato-2-butanone, b.p. (0.04 mm), 52° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe separated potassium bromide was filtered under suction
  3. washback-washed with a small amount of acetone
  4. customevaporated to dryness in vacuo at 50° C
  5. washof ether and washed three times with 100 ml
  6. dry with materialThe ether phase was dried over sodium sulfate
  7. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-aaa4ace4addd40f2a309186154684fdb
Source dataset
uspto-grants-1981_03
Patent number
US04255436

Reaction notes

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