Dimethylformamide → 2-fluoro-3-iodobenzaldehyde

HRID 352173Notes

Reaction equation

HRID 352173 reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[I:20].CN([CH:24]=[O:25])C>C1COCC1.O.C(O)(=O)C>[F:13][C:14]1[C:15]([I:20])=[CH:16][CH:17]=[CH:18][C:19]=1[CH:24]=[O:25]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 676731-Fluoro-2-iodobenzeneHCID 178418339Butyllithium

Product 1

HCID 227141892-fluoro-3-iodobenzaldehyde

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of diisopropylamine (10.42 mL, 74.36) in THF (135 mL) under N2 in an ice bath at 0-5° C. was added dropwise over 10 min n-BuLi (42.25 mL, 67.6 mmol) and stirred at this temperature for 10 min. Cooled the reaction mixture to −78° C. in a dry ice/acetone bath and dropwise added 1-fluoro-2-iodobenzene (7.88 mL, 67.6 mmol) over 5 min. Stirred at this temperature for 1 h, dropwise added DMF (6.26 mL, 74.36 mL) over 5 min, and stirred for 10 min. Added Acetic Acid (13.5 mL) followed by H2O and extracted with Et2O (2×). The combined organic solution was washed (0.1 N HCl then brine), dried (MgSO4), filtered and concentrated. The crude benzaldehyde (16.9 g) was taken onto the next step without purification. 1H NMR was consistent with structure.

Workup

  1. stirringStirred at this temperature for 1 h
  2. stirringstirred for 10 min
  3. extractionextracted with Et2O (2×)
  4. washThe combined organic solution was washed (0.1 N HCl
  5. dry with materialbrine), dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude benzaldehyde (16.9 g) was taken onto the next step without purification

Sources & evidence

ORD record
ord-20fe598c9e6344619bd901da05639a3e
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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