2-Bromo-6-nitrotoluene → 84385-64-8

HRID 1502087Notes

Reaction equation

HRID 1502087 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH3:11].[B-](F)(F)(F)[CH:13]=[CH2:14].[K+]>C(O)C>[CH3:11][C:3]1[C:2]([CH:13]=[CH2:14])=[CH:7][CH:6]=[CH:5][C:4]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 1235372-Bromo-6-nitrotolueneHCID 23679353Potassium vinyltrifluoroborate

Product 1

HCID 1285309384385-64-8

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Bromo-2-methyl-3-nitrobenzene (5.00 g, 23.1 mmol), potassium trifluoro(vinyl)borate (5.00 g, 37.3 mmol)), TEA (6.45 mL, 46.3 mmol) and PdCl2(dppf)-CH2Cl2Adduct (0.945 g, 1.157 mmol) were added to ethanol (75 mL). The mixture was degassed and then reflux for 3 hrs. The reaction was poured into brine and extracted with ETOAc. The organic layer was separated, dried over Na2SO4, filtered then concentrated. The residue was purified by chromatography on a 330 g ISCO Redi-Sep column using ethyl acetate/hexane solvent system to yield 2-methyl-1-nitro-3-vinylbenzene.

Workup

  1. customThe mixture was degassed
  2. temperaturereflux for 3 hrs
  3. additionThe reaction was poured into brine
  4. extractionextracted with ETOAc
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthen concentrated
  9. customThe residue was purified by chromatography on a 330 g ISCO Redi-Sep column

Sources & evidence

ORD record
ord-edb32d4fae5f413b8ca0bc95c277bf18
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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