2-iodo-3-methyl-benzoyl Chloride → (2-Iodo-3-methylphenyl)methanol

Temperature

-78 °C

2-Iodo-3-methyl-benzoyl chloride (1360 mg, 4.86 mmol, Example 131: a) was dissolved into THF (2 mL) and cooled to −78° C. To this was slowly added a slurry of lithium aluminum hydride (184.3 mg, 4.86 mmol) that was carefully weighed into a dry flask and cooled to 78° C., before THF (2 mL) was added. The reaction was warmed to RT slowly and stirred for an hour. The reaction was quenched by cooling back to −78° C. and adding 200 μL water, 200 μL 15% NaOH, 600 μL water and then poured over celite and filtered with THF. The title compound was obtained as a yellow solid. 1H-NMR (CDCl3): δ 7.21–7.19 (m, 2H), 7.14–7.11 (m, 1H,), 4.61 (s, 2H), 2.43 (s, 3H).

1. customwas carefully weighed into a dry flask
2. additionwas added
3. temperatureThe reaction was warmed to RT slowly
4. customThe reaction was quenched
5. temperatureby cooling back to −78° C.
6. additionadding 200 μL water, 200 μL 15% NaOH, 600 μL water
7. additionpoured over celite
8. filtrationfiltered with THF

ORD record

ord-8655eb265f7a47fb9f39bfd77f03b2c4

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07109354B2