Bromoterephthalic acid → (2-Bromo-4-hydroxymethylphenyl)methanol

Under a nitrogen stream, to a solution of 2-bromo-terephthalic acid (5.0 g, 20.4 mmol) in THF (50 ml), a THF solution of BH3 (1.09 M, 74.9 ml) was added dropwise at 0° C. and the mixture was stirred at room temperature for 4 hours. After addition of THF-water (1:1) to this solution, the reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then evaporated under reduced pressure to remove the solvent. The resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:2)) to give the titled compound (4.1 g, 92%).

1. extractionthe reaction mixture was extracted with ethyl acetate
2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
3. customevaporated under reduced pressure
4. customto remove the solvent
5. customThe resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:2))

ORD record

ord-a072c215211f4b01936d6d227fdc1b5d

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07767651B2