Hydrochloric Acid → (3-Bromo-5-iodophenyl)methanol

Temperature

0 °C

To methyl 5-bromo-3-iodobenzoate (Step A above) (5.01 g, 0.015 mole) in anhydrous methylene chloride (100 mL) at -78° C., was added dropwise minutes, diisobutylaluminum hydride (5.50 mL, 0.03 mole). The mixture was stirred for 1 hour then allowed to warm to 0° C. The reaction solution was poured into 600 mL, chilled 3N HCl and extracted 3× with methylene chloride (150 mL). The organic layers were combined, dried over MgSO4 and concentrated under vacuum to yield 5-bromo-3-iodobenzyl alcohol (4.54 g) as a white solid. MP=110-112° C. MS and NMR were consistent with the desired structure.

1. additionThe reaction solution was poured into 600 mL
2. extractionextracted 3× with methylene chloride (150 mL)
3. dry with materialdried over MgSO4
4. concentrationconcentrated under vacuum

ORD record

ord-7a3136ee0bb84c16864a250cede4929f

Source dataset

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06028223