Sodium Carbonate → (3-Bromo-2-methylphenyl)(methyl)sulfane

HRID 1879017Notes

Reaction equation

HRID 1879017 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[C:3]=1[CH3:9].[CH3:10][S-:11].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:11][CH3:10])[C:3]=1[CH3:9]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27363352-Bromo-6-fluorotolueneHCID 4378561Sodium methanethiolate

Product 1

HCID 57448061(3-Bromo-2-methylphenyl)(methyl)sulfaneYield 57.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 1-bromo-3-fluoro-2-methylbenzene (2.0 g, 10.6 mmol) in N,N-dimethylformamide (10 ml) was added sodium methanethiolate (0.85 g, 11.7 mmol) and the mixture was stirred for 15 min at 150° C. After cooling, aqueous sodium carbonate (10%, 50 ml) was added and the phases were separated. The aqueous phase was extracted with ethylacetate (2×50 ml) and the combined organic phases was dried (MgSO4) and evaporated under reduced pressure to give an oil. The residue was purified by flash column chromatography (isooctane) to give the title compound (1.33 g). MS m/z (relative intensity, 70 eV) 218 (M+, 98), 216 (M+, 92), 202 (26), 200 (26), 122 (bp), 121 (56).

Workup

  1. temperatureAfter cooling
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with ethylacetate (2×50 ml)
  4. dry with materialthe combined organic phases was dried (MgSO4)
  5. customevaporated under reduced pressure
  6. customto give an oil
  7. customThe residue was purified by flash column chromatography (isooctane)

Sources & evidence

ORD record
ord-515d9902fee94efd929005b5645a6f84
Source dataset
uspto-grants-2012_11
Patent number
US08314126B2

Reaction notes

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