Hydrochloric Acid → 2-Fluoro-3-iodo-4-methoxybenzaldehyde

HRID 2212590Notes

Reaction equation

HRID 2212590 reaction equation
[F:1][C:2]1[C:7]([I:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[CH:11]1OCC[O:12]1.Cl>CC(C)=O>[F:1][C:2]1[C:7]([I:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[CH:11]=[O:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 219664342-(2-Fluoro-3-iodo-4-methoxy-phenyl)-[1,3] dioxolane

Product 1

HCID 219664772-Fluoro-3-iodo-4-methoxybenzaldehydeYield 48.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-(2-fluoro-3-iodo-4-methoxy-phenyl)-[1,3] dioxolane (5.284 g, 16.30 mmol) in acetone (170 mL) was added HCl (1N, 170 mL) and the solution stirred at room temperature for 48 hrs. The solution was extracted with ethyl acetate and washed successively with water, brine, dried (MgSO4), filtered and evaporated. The residue was purified on silica gel (eluent: 10% ethyl acetate in hexane) to give 2.22 g of 2-Fluoro-3-iodo-4-methoxy benzaldehyde (38% for 2 steps). 1H NMR (300 MHz; CDCl3): 4.00 (s, 3 H), 6.74 (d, J=8.4 Hz, 1 H), 7.88 (t, J=8.1 Hz, 1 H), 10.21 (s, 1 H).

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. washwashed successively with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified on silica gel (eluent: 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c29e27536d2b4a968de576fb71c65369
Source dataset
uspto-grants-2006_09
Patent number
US07102000B2

Reaction notes

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