Nitric Acid → 2,6-Difluoro-3-nitrotoluene

HRID 2060669Notes

Reaction equation

HRID 2060669 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH3:9].[N+:10]([O-])([OH:12])=[O:11]>OS(O)(=O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[C:4]([F:8])[C:3]=1[CH3:9]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 5814931,3-Difluoro-2-methylbenzene

Product 1

HCID 127954862,6-Difluoro-3-nitrotolueneYield 78%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 1,3-difluoro-2-methyl-benzene (15 g, 0.12 mol) in H2SO4 (100 mL) was treated dropwise with 65% HNO3 (11.4 g, 0.12 mol) at −10° C. and the resultant mixture was stirred for about 30 min. The mixture was poured into ice-water and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo to give 1,3-difluoro-2-methyl-4-nitro-benzene (16 g, 78% yield). 1H NMR (400 MHz, CDCl3): δ 7.80 (m, 1H), 6.95 (m, 1H), 2.30 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate (3×200 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e48c420044349259785926de856ad7c
Source dataset
uspto-grants-2012_10
Patent number
US08278331B2

Reaction notes

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