Cesium carbonate → Methyl 4-chloro-3-cyclopropylmethylthio-2-methylbenzoate

HRID 548591Notes

Reaction equation

HRID 548591 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([CH3:18])[C:9]=1[SH:19].[CH:20]1([CH2:23]Br)[CH2:22][CH2:21]1>C(#N)C>[Cl:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([CH3:18])[C:9]=1[S:19][CH2:23][CH:20]1[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 67158973Methyl 4-chloro-3-mercapto-2-methylbenzoate

Product 1

HCID 67158113Methyl 4-chloro-3-cyclopropylmethylthio-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.66 g (5.09 mmol) of cesium carbonate in 20 ml of acetonitrile were added to 1.05 g (4.85 mmol) of methyl 4-chloro-3-mercapto-2-methylbenzoate. 687 mg (5.09 mmol) of cyclopropylmethyl bromide were slowly added dropwise, and the reaction mixture was stirred at RT for 16 h. For work-up, the solvent was removed, and water was added to the residue. The mixture was extracted three times with ethyl acetate, the combined organic phases were dried and filtered and the solvent was removed. What was isolated were 1.2 g of pure product.

Workup

  1. customFor work-up, the solvent was removed
  2. additionwater was added to the residue
  3. extractionThe mixture was extracted three times with ethyl acetate
  4. customthe combined organic phases were dried
  5. filtrationfiltered
  6. customthe solvent was removed
  7. customWhat was isolated

Sources & evidence

ORD record
ord-8ebbb95c94ea4562a6fc248714bd1edf
Source dataset
uspto-grants-2011_05
Patent number
US07943551B2

Reaction notes

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