1,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl ester → (5-Bromo-1,3-phenylene)dimethanol

Temperature

0 °C

To a solution of 5-bromo-isophthalic acid dimethyl ester (4.54 g, 16.63 mmol) in methylene chloride (50 mL) cooled to 0° C. under argon was added diisobutylaluminum hydride (80 mL, 80 mmol, 1 M in toluene) via syringe. The reaction was quenched by Rochelle salt solution after 1 h of stirring at 0° C. The biphasic mixture was then stirred at room temperature for 12 h before work-up. The product was extracted with diethyl ether (2×50 mL). The organic layers were washed with water, brine and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo to afford (3-bromo-5-hydroxymethyl-phenyl)-methanol as a white solid (3.582 g, 99%).

1. customThe reaction was quenched by Rochelle salt solution after 1 h
2. stirringThe biphasic mixture was then stirred at room temperature for 12 h before work-up
3. extractionThe product was extracted with diethyl ether (2×50 mL)
4. washThe organic layers were washed with water, brine
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationThe solid was then filtered off
7. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-acd1feca083f4c0d87854c773acec5f1

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06617346B1