4-Nitrobenzyl chloride → 1-Methyl-4-[(4-nitrobenzyl)sulfonyl]benzene

HRID 35862

Reaction equation

HRID 35862 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Cl)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:12]1([CH3:21])[CH:17]=[CH:16][C:15]([S:18]([O-:20])=[O:19])=[CH:14][CH:13]=1.[Na+].[K+].[Br-]>CN(C=O)C.O>[CH3:21][C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH2:8][C:7]2[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 74824-Nitrobenzyl chlorideHCID 253877Potassium BromideHCID 2723791Sodium p-toluenesulfinate

Product 1

HCID 8000821-Methyl-4-[(4-nitrobenzyl)sulfonyl]benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Nitrobenzyl chloride (5.0 g, 29.1 mmole) and sodium p-toluenesulfinate (6.8 g, 37.9 mmole) were dissolved in 50 mL of dry DMF. The mixture was stirred at about 23° for about 18 hours then diluted with water. The sulfone crystallized from the aqueous mixture and was filtered. The sulfone was purified by recrystallization from ethanol to give a pale yellow crystalline solid, mp 188°-190° (7.6 g, 25.9 mmole, 89%): IR (KBr) 2994, 1598, 1514, 1490, 1342, 1312, 1304, 1148, 824 cm-1 ; 1H NMR (CDCl3) δ 2.44 (s, 3H), 4.38 (s, 2H), 7.27 (m, 4H), 7.53 (d, J=8.3 Hz, 2H), 8.13 (d, J=8.3 Hz, 2H); MS m/e 292 (MH+).

Workup

  1. customThe sulfone crystallized from the aqueous mixture
  2. filtrationwas filtered
  3. customThe sulfone was purified by recrystallization from ethanol
  4. customto give a pale yellow crystalline solid, mp 188°-190° (7.6 g, 25.9 mmole, 89%)

Sources & evidence

ORD record
ord-910790212b3d4a7088a14695577c860d
Source dataset
uspto-grants-1995_05
Patent number
US05411969

Linked notes

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