Hydrochloric Acid → (4-Iodophenyl)(4-methoxyphenyl)methanone

4-Iodobenzoic acid (3.0 g, 11.58 mmol) was suspended in CH2Cl2 (50 mL). Oxalyl chloride (2.20 mL, 23.71 mmol) was added dropwise, followed by addition of three drops of DMF. The reaction mixture was stirred at room temperature for 3 h. CH2Cl2 and the excess of oxalyl chloride were removed under vacuum. The residue was dissolved in CH2Cl2 (35 mL) with anisole (1.70 mL, 15.41 mmol). Cooled in an ice bath, AlCl3 (2.40 g, 17.78 mmol) was added in portions. The mixture was stirred at 0° C. for 3 h, poured into 1 N HCl (50 mL) with ice, the mixture was extracted with CH2Cl2 (2×100 mL). The combined CH2Cl2 extract washed with saturated aqueous NaHCO3, brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give brown solid. The crude product was triturated with hot hexanes to give 3.91 g (98%) of compound 142 as light beige solid. 1H NMR (400 MHz, CDCl3): δ 3.89 (s, 3H), 6.96 (d, J=8.8 Hz, 2H), 7.47 (d, J=8.4 Hz, 2H), 7.79 (d, J=8.8 Hz, 2H), 7.83 (d, J=8.5 Hz, 2H). LCMS (APCI): m/z, 339 (M+H)+.

1. customCH2Cl2 and the excess of oxalyl chloride were removed under vacuum
2. temperatureCooled in an ice bath
3. stirringThe mixture was stirred at 0° C. for 3 h
4. extractionthe mixture was extracted with CH2Cl2 (2×100 mL)
5. extractionThe combined CH2Cl2 extract
6. washwashed with saturated aqueous NaHCO3, brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationthe filtrate was concentrated
10. customto give brown solid
11. customThe crude product was triturated with hot hexanes

ORD record

ord-63095ecba5244f868f44def4ebedf94c

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07569601B2