[1,1'-Biphenyl]-4-carboxylicacid, 4'-bromo-, methyl ester → [4-(4-Bromophenyl)phenyl]methanol

Temperature

0 °C

A solution of 4′-Bromo-biphenyl-4-carboxylic acid methyl ester, 7.8 g (27.9 mmol) in 150 mL of tetrahydrofuran was cooled to 0° C. via ice-water bath. Lithium aluminum hydride, 1.1 g (27.9 mmol) was added to the solution in one portion. The reaction mixture stirred at 0° C. for 1 h. The mixture was slowly quenched with 10 mL of isopropyl alcohol, then with 10 mL of water. The aqueous mixture was extracted with 3×50 mL portions of ethyl acetate. The organic layers were combined, washed with sat. aq. NaCl, and dried (MgSO4). The solution was concentrated to afford the desired product in 7.01 g (100%) as a white solid. The material was taken to the next step without further purification.

1. customThe mixture was slowly quenched with 10 mL of isopropyl alcohol
2. extractionThe aqueous mixture was extracted with 3×50 mL portions of ethyl acetate
3. washwashed with sat. aq. NaCl
4. dry with materialdried (MgSO4)
5. concentrationThe solution was concentrated

ORD record

ord-5bbcda0085a04002b3b2d7badef5ace6

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07358248B2