2,4-Difluoro-1-methylbenzene → 1,5-Difluoro-2-iodo-4-methylbenzene

HRID 1438145Notes

Reaction equation

HRID 1438145 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[I:10]N1C(=O)CCC1=O>FC(F)(F)C(O)=O>[F:8][C:6]1[CH:7]=[C:2]([F:1])[C:3]([CH3:9])=[CH:4][C:5]=1[I:10]

Participants

4

Reactant 2

HCID 679832,4-Difluoro-1-methylbenzeneHCID 120273N-Iodosuccinimide

Product 1

HCID 592835281,5-Difluoro-2-iodo-4-methylbenzeneYield 90%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 2,4-difluoro-1-methylbenzene (6 g, 47 mmol) in trifluoroacetic acid (15 mL) was added N-iodosuccinimide (12.1 g). The mixture was stirred at rt overnight before it was poured into ice and extracted with hexanes. The organic layer was separated and washed with saturated Na2S2O3, NaHCO3, brine and then dried over MgSO4. The crude product was purified by silica gel chromatography to give 94A (10.7 g, 90% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 2.15-2.30 (m, 3H) 6.73-6.85 (m, 1H) 7.55 (t, J=7.69 Hz, 3H).

Workup

  1. additionwas poured into ice
  2. extractionextracted with hexanes
  3. customThe organic layer was separated
  4. washwashed with saturated Na2S2O3, NaHCO3, brine
  5. dry with materialdried over MgSO4
  6. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-690e29d25e844f02b5b51ad2f6e85d27
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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