Iodine → 4-Iodo-1,2-dimethylbenzene

HRID 710281Notes

Reaction equation

HRID 710281 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].[I:9]I>C(Cl)Cl.FC(F)(F)S([O-])(=O)=O.[Ag+]>[I:9][C:6]1[CH:5]=[CH:4][C:3]([CH3:8])=[C:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 2

HCID 807IodineHCID 7237O-Xylene

Product 1

HCID 1416464-Iodo-1,2-dimethylbenzeneYield 78%

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,2-dimethylbenzene (1.06 g; 10 mmol), silver trifluoromethanesulfonate (2.56 g; 10 mmol) and I2 (2.53 g; 10 mmol) in CH2Cl2 (50 ml) was stirred for 7 h at room temperature, then filtered through a Celite pad, washed with fresh CH2Cl2 (2×20 ml) and combined filtrates were washed with 5% Na2SO3, H2O, brine and dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure to give crude title compound (1.8 g; 78%) as brownish oil, which was used in next step without further purification. 1H-NMR (CDCl3) 2.23 (s, 6H), 6.84 (d, 1H, J=8.0 Hz); 7.39 (dd, 1H, J=1.7; 8.0 Hz); 7.46 (broad s, 1H).

Workup

  1. filtrationfiltered through a Celite pad
  2. washwashed with fresh CH2Cl2 (2×20 ml)
  3. washwere washed with 5% Na2SO3, H2O, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e3f873ee157f4ab79c2246584636dcf2
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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