alpha-Bromo-2-nitrotoluene → HCID 23199182, compound

HRID 472438Notes

Reaction equation

HRID 472438 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6]Br)([O-:3])=[O:2].[CH3:12][S:13]([O-:15])=[O:14].[Na+]>C(O)C>[CH3:12][S:13]([CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 77569alpha-Bromo-2-nitrotolueneHCID 2733271Sodium methanesulfinate

Product 1

HCID 23199182HCID 23199182, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

164 a) A suspension of o-Nitrobenzylbromide (5.71 g, 26.4 mmol) and sodium methanesulfinate (4.0 g, 40.0 mmol) in ethanol (70 mL) was stirred at room temperature for 18 hours. The volatiles were evaporated under reduced pressure. To the residue was added water (50 mL) and stirred for 30 minutes. The suspension was filtered, rinsed with water and air dried. 1-Methanesulfonylmethyl-2-nitro-benzene was isolated as a yellow solid (5.36 g, 94%). MP=115-117° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.10 (d, J=8.1 Hz, 1H), 7.74-7.65 (m, 2H), 7.62-7.58 (m, 1H), 4.80 (s, 2H), 2.91 (s, 3H).

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. additionTo the residue was added water (50 mL)
  3. stirringstirred for 30 minutes
  4. filtrationThe suspension was filtered
  5. washrinsed with water and air
  6. customdried

Sources & evidence

ORD record
ord-cce21671c7c7436197cc311dd9890c0d
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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