Water → 1-Bromo-2-(cyclopropylsulfanyl)benzene

HRID 2192886Notes

Reaction equation

HRID 2192886 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].Br[CH:10]1[CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)S)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH:10]1[CH2:12][CH2:11]1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 78037BromocyclopropaneHCID 805982-Bromobenzenethiol

Product 1

HCID 595709161-Bromo-2-(cyclopropylsulfanyl)benzeneYield 81.4%

Reagents, catalysts & solvents 3

HCID 77281Benzenemethanethiol, alpha,alpha-diphenyl-CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-bromobenzenethiol (50 g) in DMF (500 mL) were added bromocyclopropane (41.6 g), potassium carbonate (54.8 g), and triphenylmethanethiol (1.46 g), followed by stirring at an internal temperature of 80° C. for 24 hours. After cooling to room temperature, water and ethyl acetate were added thereto, and the organic layer was then separated. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1-bromo-2-(cyclopropylsulfanyl)benzene (49.3 g).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe organic layer was then separated
  3. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-68b7b06613c94dab94e85492a5bc94aa
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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