Benzene, 1-(bromomethyl)-3-nitro- → 1-[(Cyclopropylsulfonyl)methyl]-3-nitrobenzene

HRID 1405212Notes

Reaction equation

HRID 1405212 reaction equation
[CH:1]1([S:4]([O-:6])=[O:5])[CH2:3][CH2:2]1.[Na+].Br[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1>C(#N)C.O>[CH:1]1([S:4]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 42643363Sodium cyclopropanesulfinate

Product 1

HCID 709764591-[(Cyclopropylsulfonyl)methyl]-3-nitrobenzeneYield 96.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

Sodium cyclopropanesulfinate (1.04 g; 8.1 mmol) was added to a stirred solution of 1-(bromomethyl)-3-nitrobenzene (1.17 g; 5.4 mmol) in acetonitrile (50 ml) at room temperature. The batch was stirred at 90° C. for 4 hours. After cooling, the batch was diluted with water and extracted with DCM (2×). The combined organic phases were filtered using a Whatman filter and concentrated to give the desired product (1.26 g) that was used without further purification. 1H NMR (400 MHz, CDCl3, 300K) δ=8.28 (m, 2H), 7.81 (m, 1H), 7.61 (m, 1H), 4.37 (s, 2H), 2.29 (m, 1H), 1.21 (m, 2H), 1.03 (m, 2H).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with DCM (2×)
  3. filtrationThe combined organic phases were filtered
  4. filtrationfilter
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9d82af624c584055a189654494ecca5a
Source dataset
uspto-grants-2014_12
Patent number
US08916557B2

Reaction notes

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