Dimethylformamide → 2-Fluoro-6-iodobenzaldehyde

HRID 2245282Notes

Reaction equation

HRID 2245282 reaction equation
C(NC(C)C)(C)C.[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([I:15])[CH:10]=1.[Li+].CC([N-]C(C)C)C.CN([CH:27]=[O:28])C>C1COCC1>[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([I:15])[C:10]=1[CH:27]=[O:28]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 707251-Fluoro-3-iodobenzeneHCID 2724682Lithium diisopropylamide

Product 1

HCID 110969762-Fluoro-6-iodobenzaldehydeYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Buthyllithium (1.6 M, 60 ml, 0.113 mol) is added to an ice cooled solution of diisopropyl-amine (17.6 ml, 0.124 mol) in THF (200 ml). The solution is stirred at 0° C. for 30 minutes and is cooled to −78° C. 1-Fluoro-3-iodo-benzene (25 g, 0.113 mol) in THF (20 ml) is slowly added to the preformed LDA mixture. The resulting solution is stirred for another hour after which DMF (9.55 ml, 0.124 mol) is added and stirring is continued for another 30 minutes at −78° C. The reaction is quenched first with acetic acid (20 ml) followed by water (200 ml). The mixture is extracted with ether. The organic layer is washed with a 2N HCl solution, brine, is dried over MgSO4 and evaporated to afford the desired compound (28.3 g).

Workup

  1. temperatureis cooled to −78° C
  2. additionis added
  3. stirringstirring
  4. waitis continued for another 30 minutes at −78° C
  5. customThe reaction is quenched first with acetic acid (20 ml)
  6. extractionThe mixture is extracted with ether
  7. washThe organic layer is washed with a 2N HCl solution, brine
  8. dry with materialis dried over MgSO4
  9. customevaporated

Sources & evidence

ORD record
ord-9d012ab647574a73b5aa93397c2114a7
Source dataset
uspto-grants-2010_03
Patent number
US07683075B2

Reaction notes

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