Ethyl 4-iodobenzoate → 4-Iodobenzyl alcohol

Temperature

0 °C

A stirred, cooled (−78° C.) solution of ethyl-4-iodo-benzoate (available from Lancaster, 12.9 g, 45 mmol) in anhydrous dichloromethane (100 mL) under argon was treated with a 1M solution of di-isobutyl aluminum hydride in dichloromethane (100 mL, 100 mmol). The reaction mixture was allowed to warm to 0° C. in 1.5 h, quenched with saturated aqueous ammonium chloride solution and the resulting emulsion was filtered over a bed of celite. The phases in the filtrate were-separated and the aqueous phase was extracted with dichloromethane (×1). The combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford the title product as a white solid (9 g, 85%).

1. customquenched with saturated aqueous ammonium chloride solution
2. filtrationthe resulting emulsion was filtered over a bed of celite
3. customThe phases in the filtrate were-separated
4. extractionthe aqueous phase was extracted with dichloromethane (×1)
5. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
6. filtrationfiltered
7. customevaporated in vacuo

ORD record

ord-5dd84c400938409fa49a8786745b3caa

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07226951B2