Formic Acid → N-(2-fluoro-4-iodophenyl)formamide

HRID 2427332Notes

Reaction equation

HRID 2427332 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[C:10](OC(=O)C)(=[O:12])C.C(O)=O>O1CCCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C.Cl>[F:9][C:4]1[CH:3]=[C:2]([I:1])[CH:8]=[CH:7][C:5]=1[NH:6][CH:10]=[O:12]

Participants

8

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 1856942-Fluoro-4-iodoaniline

Product 1

HCID 23549341N-(2-fluoro-4-iodophenyl)formamideYield 97.1%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cooled solution (0° C.) of 4-iodo-2-fluoroaniline (3.05 g, 12.9 mmol) in tetrahydrofuran (15 mL) and toluene (15 mL), was slowly added a mixture of acetic anhydride (1.39 mL, 14.7 mmol) and formic acid (0.83 mL, 22.0 mmol). The reaction mixture was stirred at rt overnight, then diluted with ethyl acetate (100 mL) and 1N aqueous HCl (100 mL). The layers were separated, and the organic layer was washed with water and saturated sodium carbonate solution, and dried over sodium sulfate. The solvent was removed under reduced pressure to afford 2-fluoro-4-iodophenylformamide as an off-white solid (3.32 g, 97%). GC-MS ret. time 2.27 min, m/z 265 (M+); 1H NMR (300 MHz, CDCl3) δ: 7.37-7.51 (m, 3H), 8.13 (t, 1H), 8.46 (s, 1H).

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with water and saturated sodium carbonate solution
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cd11e9e96f9d4283be4a0275faf835bb
Source dataset
uspto-grants-2011_06
Patent number
US07968576B2

Reaction notes

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