Formic Acid → n-(4-Iodophenyl)formamide

To a solution of 4-iodoaniline (30.0 g, 137 mmol) in 100 mL THF and 100 mL toluene, a solution of acetic anhydride (16.0 g, 157 mmol) and formic acid (10.8 g, 235 mmol) was slowly added from an addition funnel under argon atmosphere. The reaction mixture temperature was maintained below 15° C. during the addition. After the addition was finished, the reaction mixture was stirred at rt overnight. The reaction mixture was diluted with water (300 mL) and ethyl acetate (200 mL). The organic layer was separated, washed with water (2×200 mL), and 200 mL saturated aqueous sodium bicarbonate solution. After drying over sodium sulfate, the mixture was concentrated under reduced pressure to afford 4-Iodoformanilide as an off-white solid (33.5 g, >98%). 1H NMR (DMSO-d6) δ 10.27 (s, 1H), 8.26 (d, J=2 Hz, 1H), 7.64 (d, J=12 Hz, 2H), 7.40 (d, J=11.7 Hz, 2H) and 30% tautomer; ESI-MS m/z 248.0 (MH+).

1. temperatureThe reaction mixture temperature was maintained below 15° C. during the addition
2. additionAfter the addition
3. customThe organic layer was separated
4. washwashed with water (2×200 mL), and 200 mL saturated aqueous sodium bicarbonate solution
5. dry with materialAfter drying over sodium sulfate
6. concentrationthe mixture was concentrated under reduced pressure

ORD-Eintrag

ord-3117c94e8c2e4eec9d869a0c62704a73

Quelldatensatz

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07091228B2