Ethanethiol → (2-Bromo-4-nitrophenyl)(ethyl)sulfane

HRID 1438151Notes

Reaction equation

HRID 1438151 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[CH2:12]([SH:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[S:14][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 696992-Bromo-1-fluoro-4-nitrobenzene

Product 1

HCID 57942894(2-Bromo-4-nitrophenyl)(ethyl)sulfaneYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 3-bromo-4-fluoronitrobenzene (7.05 g, 32.0 mmol) and ethanethiol (2.6 mL, 35.2 mmol) in DMF (20 mL) was added potassium carbonate (4.87 g, 35.2 mmol). The reaction mixture was heated to 60° C. overnight. After cooling, the mixture was filtered over celite and washed with ethyl acetate. The combined filtrate and washings were concentrated. The residue was redissolved in ethyl acetate and washed with water (3×) and then dried over sodium sulfate. The filtrate was concentrated and purified by flash column chromatography to give 100A (8.09 g, 96% yield) as a solid. 1H NMR (400 MHz, Methanol-d4) δ ppm 1.41 (t, J=7.34 Hz, 3H) 3.11 (q, J=7.42 Hz, 2H) 7.45 (d, J=9.05 Hz, 8H) 8.17 (dd, J=8.80, 2.45 Hz, 7H) 8.37 (d, J=2.45 Hz, 7H).

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered over celite
  3. washwashed with ethyl acetate
  4. concentrationThe combined filtrate and washings were concentrated
  5. dissolutionThe residue was redissolved in ethyl acetate
  6. washwashed with water (3×)
  7. dry with materialdried over sodium sulfate
  8. concentrationThe filtrate was concentrated
  9. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-f06e5ad10b2b45f484a8b06dde4e4a23
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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