Methanol → Methyl 5-fluoro-2-iodobenzoate

Temperature

65 °C

To a 500 mL round-bottomed flask was added 5-fluoro-2-iodo-benzoic acid (23 g, 86.5 mmol) in methanol (230 mL). To the resulting solution was added conc. sulfuric acid (2.3 mL, 43.2 mmol). The reaction mixture was warmed to 65° C. and stirred for 15 h. The resulting mixture was concentrated under reduced pressure to give crude product which was then was partitioned between EtOAc (250 mL) and a half sat. Na2CO3(aq) solution (250 mL). The layers were thoroughly mixed and then separated. The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give a yellow oil (23 g, 95% yield). 1H NMR (400 MHz, CDCl3): 7.94 (dd, J=8.7, 5.4 Hz, 1H), 7.54 (dd, J=9.0, 3.1 Hz, 1H), 6.93 (m, 1H), 3.94 (s, 3H).

1. concentrationThe resulting mixture was concentrated under reduced pressure
2. customto give crude product which
3. customwas then was partitioned between EtOAc (250 mL)
4. additionThe layers were thoroughly mixed
5. customseparated
6. dry with materialThe organic layer was dried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-9b2fd062af7442f79cc268752d9a8b6e

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653263B2